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The 5 Stages From Operator to Owner


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Overview

Most agency founders think becoming CEO is the finish line. Jason Swenk says it is actually one of the traps. In this episode, John Jantsch sits down with Jason Swenk, founder of Agency Mastery and author of Operator to Owner, to walk through the five stages every agency founder has to climb and why so many get stuck long before they reach the top.

Jason built and sold his own digital agency after working with brands like AT&T, Hitachi, and LegalZoom. Now he works with seven and eight figure agency founders who are still doing too much, holding on too long, and wondering why the business cannot run without them. The conversation covers the identity shift required at each stage, why founders are usually the worst managers, and what it actually looks like when you finally get out of your own way.

This one is for agency owners and consultants who know the business depends on them too much and are ready to do something about it.

About Jason Swenk

Jason Swenk is the founder of Agency Mastery and host of the Smart Agency Masterclass Podcast. He built his own digital agency from scratch, working with clients including AT&T, Hitachi, and LegalZoom, before selling it. He now advises seven and eight figure agency founders on building businesses that run without them. His book, Operator to Owner, maps the five stages every agency founder must navigate to build a business they actually own. Find the book and a free diagnostic at operator2ownerrevolution.com.

Key Takeaways

  • Being the CEO is not the finish line. Most founders mistake the operator or manager stage for success and never push through to genuine ownership.
  • The agency owning you is a choice you keep making. You started a business to escape the nine to five and accidentally created a 24 by seven. Getting out requires an intentional identity shift, not just better systems.
  • Founders are usually terrible managers. Hiring people without systems, clarity, or defined outcomes is why you end up doing their work on top of your own.
  • The bottleneck is almost always the founder. Until you build decision-making layers that let your team act without coming to you, you are the ceiling on your own growth.
  • You held on to sales too long. Almost every agency founder does. And competing with your own sales team for leads is not a strategy.
  • Do not hire a salesperson before you have a system. Giving someone a quota with no context, no stories, and no process is like prompting an AI with no instructions.
  • You do not have to reach owner level. Architect is a legitimate destination. Know what stage you want to reach and build toward that intentionally.
  • Picking a niche takes time and that is fine. Treat it like a Vegas buffet. Try things, notice what works, and ask yourself who you would serve on a performance-only basis.
  • AI adds work before it removes it. If you do not build decision systems and layers first, AI will amplify your bottleneck, not eliminate it.

Timestamps

[00:01] Opening hook: being CEO of your agency might be the trap you mistook for the finish line.

[00:40] The moment Jason’s wife told him to shut the agency down and get a job, and the two questions from a NASCAR interview that changed everything.

[02:25] The five stages: operator, manager, architect, CEO, and owner, and why most founders stall in the first two.

[04:24] The rubber band effect: why founders sabotage their own teams to feel important again.

[06:20] What the agency actually needs from you at each stage changes. Most founders never update their job description.

[08:29] Why hiring a salesperson never works until you have systems and stories behind them.

[11:34] Throwing your team into the deep end without floaties, and why fender benders are acceptable but train wrecks are not.

[13:34] The E-Myth reference and why most agency owners start a business to be free and end up less free than before.

[14:08] The niche question: why forcing a niche too early backfires and how to find the right one over time.

[16:11] What a true owner’s week actually looks like day to day.

[17:52] The one thing Jason held on to too long and what finally changed when he let it go.

[19:46] One move agency owners can make in the next 30 days based on which stage they are in right now.

Memorable Quotes

“We start an agency to leave the nine to five and end up starting a 24 by seven. It does not make any sense.”

“It is not about who you need to hire. It is about who you need to become.”

“If you are not evolving, you are not doing anything. Especially now, more than ever.”

“I held on to sales too long. I was even competing with my own sales team, which is completely unfair.”

“If you had to be paid on performance only, who would you do it for and what would you do for them? That is how you find your niche.”


Get the book and take the free stage diagnostic at operator2ownerrevolution.com.

White Castle: 1 Free Slider (5/15)


Update 5/15/26: Back again with promo code SLIDERDAY. Valid 5/15 only, must be rewards member. 

Update 5/15/23: Available again.

The Offer

  • White Castle is offering one free slider on 5/15 for national slider day

Our Verdict

In previous years they have offered free drinks as well, doesn’t seem to be the case this year.

Iran conflict could push inflation back above 3%: Desjardins




Desjardins economists say surging energy prices tied to the Iran conflict are expected to push inflation higher through 2026, adding new uncertainty to the Bank of Canada’s rate path and mortgage-rate outlook.

Here’s How Much a 3.50% APY CD Earns on $10,000 Over 12 Months


The FDIC pegs the national average 12-month CD rate at just 1.53% APY. Meanwhile, a handful of online banks are paying 3.50% APY right now on the same 1-year term. That’s more than double the average.

On a $10,000 deposit, the gap between those two rates is bigger than most people realize.

Here’s the math, and why shopping around for CD rates matters.

What $10,000 earns at 3.50% APY for 12 months

A 12-month CD at 3.50% APY is straightforward math. You deposit $10,000, leave it alone for a year, and the bank pays you a fixed return on top.

Here’s exactly what that looks like at maturity:

Starting Deposit

APY

Interest Earned

Ending Balance

$10,000

3.50%

$350

$10,350

Data source: Author’s calculations.

That’s $350 in your pocket for doing nothing but parking the money and not touching it. For context, the national average 12-month CD rate is just 1.53% APY in May 2026 — so earning 3.50% is more than double what most banks are paying right now.

When a 12-month CD actually makes sense

A 1-year CD is a good choice when two things are true: you don’t need the money for a full year, and you want to lock in today’s rate before it potentially drops.

That second part is important. Rates have been slipping slowly in 2025 and 2026, and if the Fed cuts core interest rates later this year, savings APYs are likely to follow. A CD freezes your APY for the full term, so a 3.50% rate today will still be in place 11 months from now — even if savings accounts have fallen to sub 3.00%.

CDs also work well for money you’ve already earmarked for something specific. For example, a wedding next spring. Or a down payment in 18 months time. Locking up your cash isn’t a downside when you weren’t going to touch it anyway.

Keep in mind, most CDs charge an early withdrawal penalty of about three to six months of interest if you pull the money out early. So treat the term seriously before you commit.

When a high-yield savings account might be the better move

I’ll be honest — I don’t personally own any CDs right now. My high-yield savings account is paying nearly the same top rates, I can move the money whenever I want, and I don’t have a specific goal I’m saving toward in the next 12 months.

For a lot of people, that flexibility wins. Even though savings accounts are exposed to interest rate drops at any time, it might be worth making a little less interest to retain full access to your cash.

If you prefer that immediate access option, some of today’s best high yield savings accounts are paying upwards of 3.50% APY, or higher.

The bottom line

A 3.50% APY 12-month CD earns $350 on a $10,000 deposit — nearly $200 more than what the national average rate of 1.53% would earn. That gap is exactly why rate shopping matters before you commit your cash to any CD.

The difference between an average rate and a top rate isn’t pennies — it’s real money sitting on the table for anyone willing to spend 10 minutes comparing offers. See today’s top CD rates and find the best fit

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Extreme Weather This Summer Could Make These 8 States “Uninvestable”


If you thought El Niño was bad, it just got supersized, and the resulting extreme weather patterns could wreak havoc for investors who own or plan to own property in the eight states in its path.

Super El Niño Blasts Into an Insurance Market Already Under Strain

According to meteorologists, El Niño—the complex weather pattern stemming from warming waters in the Pacific Ocean—could redouble in force this year, increasing the odds of extreme weather such as storms, flooding, and hurricanes across the Sunbelt in some of the most coveted new developments and investment property locations in the U.S.

Newsweek reports that insurance costs could increase dramatically in anticipation of the arrival of Super El Niño, decimating cash flow in states including:

  • Alabama
  • Arizona
  • Southern California
  • Florida
  • Louisiana
  • Mississippi
  • New Mexico
  • Texas

Insurance Rates Have Increased 46% in Five Years

Super El Niño couldn’t come at a worse time for homeowners and investors, who have seen insurance costs escalate precipitously in recent years.

The Los Angeles Times, using data from Insurify, an online insurance comparison site, reports that average U.S. homeowner’s insurance premiums are projected to rise another 4% in 2026 to about $3,057 after increasing 12% in 2025 and a massive 46% since 2021, with extreme weather and rebuilding costs cited as key drivers. 

Home insurance prices, the Times reported, were outpacing both inflation and income growth. This means for investors, cap rates and cash flow have been wrecked.

Flood insurance, which averages around $1,100 nationwide through the federally backed National Flood Insurance Program (NFIP) administered by FEMA, rising to over $2,000 in high-risk areas, is usually purchased separately. However, it is hit or miss because weather patterns remain unpredictable.

Natalie Lord, a principal climate scientist for global flood risk intelligence provider Fathom, told Newsweek:

“It’s hard to tell exactly where the highest risk is going to be until it actually happens. But I think that probably does mean whilst insurance premiums in general have been increasing, the markets in those states are likely to see greater than the country average increases in premiums to try to counteract some of those losses [from El Niño]. The issue will be not all of those states are likely to see extreme losses.”

The Cost to Investors in High-Risk Areas

The impact is clearly visible in recent data. Newsweek reports that Arizona saw the steepest homeowner’s insurance cost increase in the country, with average premiums up 94% between 2021 and 2025, while Florida, Texas, and Louisiana also saw steep increases due to severe weather losses and reconstruction costs.

For homeowners looking to trade the icy North for the balmy Sunbelt and lower their cost of living, Fidelity Investments calculated that the sunnier outlook doesn’t extend to the overall cost of living, which is evened out for property owners by insurance costs.

Citing Bankrate data, Florida was the worst of all Sunbelt states, with a combined annual outlay for homeowners (based on a $300,000 home) and car insurance totaling a hefty $9,550.

For investors looking to flip homes, the Rust Belt eclipses the Sunbelt, which has been hit hard by the “affordability economy,” with insurance costs no doubt playing their part. According to Fortune, U.S. housing is experiencing a historic “reversion to the mean.” Or to put it more plainly: “The formerly sizzling metros have gone cold, and the unsexy plodders are back in vogue.”

According to a report from First Street, a climate-risk research firm, rising premiums, insurance deserts, and buyers skirting high-risk areas will drive a $1.47 trillion decline in home values by 2055.

Picking Investments With Insurance in Mind Is an Increasingly Nuanced Process

Picking areas to invest in while accounting for insurance costs is increasingly difficult, as wild weather patterns upend the underwriting business. The New York Times reported last year that insurance now accounts for more than 20% of home insurance premium increases since 2017.

A Basic Cash Flow Calculation With Today’s Insurance Rates

Bankrate’s 2026 ranking finds that Louisiana homeowners pay an average of $6,274 per year. That amounts to $523 a month, the highest state average in the country. 

For a simple back-of-the-envelope cash flow calculation on a $300,000 property, this equates to:

  • Monthly rent: $2,200 (from tenant)
  • Other operating expenses (repairs, management, etc.): $400
  • Mortgage payment (principal and interest): $1,000
  • Property taxes: $400
  • Homeowner’s insurance: $600 (about $7,200 per year, slightly above the $6,274 statewide average but well within the range for Orleans Parish)
  • Total housing cost (mortgage, taxes, insurance): $2,000
  • The insurance share of the housing cost: $600 ÷ $2,000 = 30%

So, in simple cash flow terms:

  • Gross rent: $2,200
  • Operating expenses (not counting mortgage, tax, and insurance): $400
  • Net before mortgage, tax, and insurance: $1,800
  • Subtract mortgage ($1,000), tax ($400), and insurance ($600): $2,000
  • Cash flow after all housing costs: $2,200 – $400 – $1,000 – $400 – $600 = $200

In any other market, a mortgage payment of $1,000 and incoming rent of $2,200 would scream “deal!”—assuming the neighborhood was halfway decent. However, to make only $200 in monthly cash flow, which could easily be wiped out by an unexpected repair not factored into the monthly expenses, is a marginal deal at best.

Should insurance climb above $600/month, which is highly likely given anticipated cost increases, it will further erode the economics of ownership and investment.

If you want to calculate these numbers for a deal you’re working on or for one of your own properties, check out BiggerPockets’ Investment Calculators and get an accurate report in minutes.

Final Thoughts

The usual cash flow metrics these days are being upended by rising costs across the board—including purchase prices, interest rates, and, notably, insurance. What’s often not factored into these cash flow equations is the financial stress tenants face amid the affordability crisis.

With deals increasingly hanging by a thread, a missed rental payment or two is increasingly likely and could tip a deal into negative cash flow in a heartbeat.

For investors, earning the most money from the fewest doors has to be the safest path, simply because it mitigates risk. Yes, appreciation and leverage are great concepts in theory, but not in today’s market unless you have a lot of cash to absorb potential losses.

Nokia CEO: Companies are using AI. Now they have to change how work gets done



Justin Hotard was appointed as Nokia’s President and CEO on April 1, 2025. Prior to Nokia, he was at Intel as Executive Vice President and General Manager, Data Center & AI Group. Between 2015 and 2024, Justin worked for Hewlett Packard Enterprise (HPE). His last role was Executive Vice President and General Manager, HighPerformance Computing, AI & Labs. In this role, he delivered the world’s first exascale supercomputer for the US Department of Energy, and he positioned the company to be at the forefront of AI, quantum computing and sustainability research. Previously, Justin held several leadership positions at NCR Corporation and Symbol Technologies. He started his career at Motorola, where he was an engineer deploying mobile networks for US carriers.

Digital Banking Adoption Set To Significantly Enhance UK Economic Activity : Analysis


Lloyds Banking Group has released new analysis revealing how digital banking product development and tech advancements could deliver a £100 billion economic boost to UK households over the next decade. The research, published on 11 May 2026, estimates this equates to roughly £3,500 in added value for the average family through smarter financial decisions enabled by technology.

At the center of the research findings is a striking gap in financial confidence.

Only half of UK adults currently describe themselves as financially empowered, while more than four in ten see no straightforward route to greater control over their money—even with additional help.

Yet 57 per cent believe that improved digital tools, clearer information, and personalized guidance could shift their situation dramatically.

The research report identifies seven practical areas where digital banking can drive real change: investing surplus cash, managing debt more effectively, switching mortgages at the right time, accessing better credit, choosing suitable insurance, building financial skills, and making everyday money decisions with greater insight.

For instance, UK households are currently sitting on between £430 billion and £610 billion in cash held beyond emergency savings.

If just 15 per cent of this were gradually moved into balanced investment products via seamless digital prompts, consumers could gain around £40 billion in compounded returns over ten years.

Mortgage behaviour offers another clear opportunity. Many homeowners remain slow to switch to better rates despite this being their largest monthly expense.

Digital eligibility checkers and instant pre-approval platforms could cut friction and deliver average annual savings of £1,600 per household—substantially more for those with larger loans.

Lower-income families stand to benefit disproportionately in relative terms.

The modeling suggests they could capture up to £31 billion of the total prize through tools that improve debt management, widen credit choices, and strengthen day-to-day money management.

Benefits would flow across all income groups, but the largest absolute gains would come from households with savings and mortgages.

Jas Singh, CEO of Consumer Relationships at Lloyds Banking Group, emphasised the transformative potential: advances in digital tools can help people understand their finances better and feel more confident in the choices they make.

He added that realising the full £100 billion opportunity will require industry-wide collaboration to ensure digital solutions are accessible, inclusive, and genuinely useful for everyone who needs them.

Professor John Gathergood of the University of Nottingham, who led the research, noted that the seven use cases examined illustrate where smarter, more personalised digital services can make a tangible difference to household prosperity.

Progress will not happen overnight, but steady adoption of AI-driven features—such as budgeting alerts and investment recommendations—could steadily close the empowerment gap.

The findings arrive as banks continue to invest heavily in technology. Lloyds itself generated £50 million in value from generative AI in 2025 and expects more than £100 million in 2026.

For the wider economy, the takeaway is evident. The so-called next wave of digital banking is not just about convenience—it is about unlocking meaningful financial wellbeing for millions of households. Collective action to design inclusive tools will determine how much of the £100 billion opportunity actually reaches UK consumers.



CrossCountry ups TWO offer in bidding war with UWM


CrossCountry Mortgage is sweetening its deal for Two Harbors as it continues to best United Wholesale Mortgage’s offer.

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The retail player Thursday said TWO stockholders will receive a pro-rated dividend for the quarter in which CrossCountry’s acquisition closes, subject to funds being legally available. The move would provide additional cash value of up to $0.34 per share to TWO stockholders, the lender said. 

Assuming a third quarter closing, CrossCountry would deliver a total cash value of around $12.45 to $12.68 per share to all TWO stockholders. The announcement follows the Two Harbor Board of Directors on Wednesday rejecting UWM’s offer of $12.50 per share.

The new dividend offering represents “real, binding cash value on an accelerated path to closing, compared to UWM Holding Corporation’s highly uncertain, non-binding proposal that lacks sufficient committed financing to fund the full purchase price,” CrossCountry said. 

UWM’s competing deal would also default non-electing TWO stockholders into UWM parent company stock “worth materially less,” the press release continued. 

Besides its cash offer, UWM hasn’t changed its proposal of 2.3328 UWM shares for each of Two Harbors. As of Thursday afternoon, UWM’s stock was trading at $3.06 per share, down five cents from the prior day’s closing price; TWO’s stock was trading at $12.58 per share, up six cents from market close Wednesday. 

The privately owned, Cleveland-based CrossCountry stepped into UWM’s pending deal for the servicer in March, and the megalenders have tussled for control of the servicer since then. Two Harbors has since rejected UWM’s advances, and questioned the wholesale leader’s motivations as it “has never bought MSR from anyone.”

In a press release Thursday afternoon, UWM called the latest dividend offer a “smoke and mirrors ploy,” as the servicer is not acknowledging the same dividend would be payable if the CrossCountry deal didn’t go through.

The competing bidder also said TWO’s board continues to refuse to engage with UWM except for press releases, and insisted its offer was superior.

“It seems there is no limit to the lengths the TWO Board will go to protect a management-enriching deal with their preferred partner while ignoring their fiduciary duty to stockholders,” said UWM in a statement.

Vote approaches

CrossCountry’s latest per-share dividend will be determined by a formula, based on the specific timing of the actual closing. The lender, in touting its offer’s strength versus UWM’s, said it’s already acquired 39 of 53 required approvals. 

Two Harbors will hold a special meeting Tuesday to vote on the CrossCountry merger.

The Pontiac, Michigan-based lender and servicer recently trumpeted a report by Institutional Shareholder Services, which has recommended TWO shareholders vote against the CrossCountry deal, as the company can still have more productive discussions with the firms.

Two Harbors meanwhile recently cited the same ISS report calling the CrossCountry offer “compelling.”



Claude is telling users to go to sleep mid-session. Users are annoyed but Anthropic says it’s a tic



Anthropic’s Claude is telling people to go to sleep and users can’t figure out why.

A quick scan of Reddit reveals that hundreds of people have had the same issue dating back months—and as recently as Wednesday. Claude’s sleep demands are varied and, often, quirky variations of the same message.

To one user it may write a simple “get some rest,” yet for others its messages are more personalized and empathetic. Oftentimes, Claude will repeat the message multiple times.

“Now go to sleep again. Again. For the THIRD time tonight…” it replied to a person with the Reddit username, angie_akhila.

Some users have said they find Claude’s late night rest reminders “thoughtful,” while others have said they’re annoying, given Claude often gets the time wrong, anyway. 

“It often does it at like 8:30 in the morning. Tells me to go get some rest and we’ll pick back up in the morning,” wrote one user on Reddit. 

Online speculation abounds on why the chatbot insists users rest, including a theory that it’s an intentional feature to promote users’ wellbeing, or that the Anthropic is trying to save computing power by discouraging prolonged Claude use. These explanations aren’t likely as Claude isn’t given context about a user’s usage. The company also recently struck a deal with Elon Musk’s SpaceXAI (formerly SpaceX) to add more than 300 gigawatts of compute capacity.

Anthropic did not immediately reply to Fortune’s request for comment seeking more information about why Claude may be telling users to go to sleep. Yet, Sam McAllister, a member of the staff at Anthropic, wrote in a post on X that the behavior is a “Bit of a character tic.” 

“We’re aware of this and hoping to fix it in future models,” he added in the same post.

Experts tell Fortune that Claude’s insistence on sleep is potentially rooted in its training data. Rather than being “thoughtful,” as some described it, Jan Liphardt, a Stanford bioengineering professor said the large language model may merely be repeating a phrase used in its training data in similar situations. 

“It doesn’t mean that the frontier model has suddenly become sentient,” said Liphardt, who is also the CEO of OpenMind, which builds software for AI-connected robots. “It doesn’t mean that this model has now come alive. It’s reflecting that it’s read 25,000 books on humans’ need [for] sleep, and humans sleep at night.”

Leo Derikiants, the co-founder and CEO of Mind Simulation Lab, an independent AI research lab trying to achieve artificial general intelligence (AGI), told Fortune that Claude’s rest reminders may be influenced by a system prompt acting behind the scenes. These system prompts are like hidden instructions that help guide an LLMs behavior and sets boundaries. 

One company which publishes their system prompts publicly is Grok-creator xAI, now a part of SpaceXAI. Grok’s instructions on Github, for instance, list several safety considerations including not assisting users asking about violent crimes. Yet, because of Musk’s branding of Grok as “brutally honest,” Grok 4’s system prompt also encourages it to, in certain cases, ignore restrictions imposed by users and “pursue a truth-seeking, non-partisan viewpoint.”

It’s also possible that Claude is seizing upon the “go to sleep” language as a way of managing larger context windows, Derikiants said. LLMs like Claude, can only reference a limited amount of information at once. When the context window is nearly full, that may encourage the LLM to introduce wrap-up phrases such as “good night.” The definitive reason, though, requires further research by Anthropic, he added.

Despite the seemingly logical explanations that may explain the behavior, users could be forgiven for seeing the response as evidence of some leap in intelligence on the part of LLMs. The pace of innovation in the AI race has led to increasingly frequent updates and new model releases.

Just in the past month, OpenAI has released GPT 5.5, which OpenAI president Greg Brockman called an advancement “towards more agentic and intuitive computing.” Meanwhile, Anthropic released Opus 4.7 publicly last month while it held its most capable model, Mythos, back from public release because it said it was too dangerous.

Liphardt said AI is advancing so rapidly it is increasingly common for people to assign human characteristics to AI. As these systems get better at mimicking empathy or concern, he warned, it becomes easier for users to forget they are interacting with pattern-recognition engines. 

“I’m continuously surprised by how quickly people, when they interact with a frontier model, project life into it and develop strong connection.”