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I’m a CEO who’s run 18 Ironman races and the AI ROI race isn’t any different

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I’ve spent two decades competing in Ironman Triathlons, grueling, single-day events that total over 140 miles. I’ve spent even longer leading high-growth companies, from Google and Dropbox to Freshworks. 

You could say that I’ve been operating with a need for speed my entire adult life. And if there’s one thing these experiences have taught me, it’s that most companies are pacing the AI race all wrong.

Recent data from Bain & Company shows that 95% of U.S. companies are using generative AI in some form, yet only 5% of firms see meaningful value from their AI investments. 

I believe this is happening because, like rookie triathletes, many business leaders treat AI like a sprint – chasing speed, hype, and short-term wins, while expecting long-term, sustainable results. In both racing and business, success hinges on pacing yourself, building stamina, and staying focused on the long game.

The Ironman playbook for AI

Over my 18 Ironmans, I’ve learned that the real key isn’t strength or speed – it’s structure. Whether training for race day or leading a company through AI transformation, you need a set of principles to keep you grounded and disciplined through uncertain (and sometimes fatiguing) times. The three I stand by are:  

  1. Play to your strengths 
  2. Uncomplicate to scale  
  3. Consistency over chaos

As a CEO, these principles have guided me in building, scaling, and leading through one of the most disruptive shifts the SaaS industry has seen in decades.
 

Play to your strengths  
In my first few Ironman races, I tried to keep up with the veterans in the swim. Big mistake. I burned too much too soon and paid for it the rest of the way. Eventually, I learned that performance – in racing or business – isn’t about matching someone else’s speed. It’s about knowing your strengths, then pacing with purpose and trusting your own race plan.

The same lesson applies in setting an AI strategy. Every company wants to mimic the playbooks of the Googles or OpenAIs of the world. But not every company should — and that’s not a bad thing. As much as I admire my former colleagues at Google, we’re not trying to emulate them. Our race is different. Our landscape, resources, and goals aren’t the same.

The leaders of the AI race are the ones who know who they are and who they are not. Not every organization needs to become an AI research lab, developing new models and infrastructure from scratch. The best leaders will use AI to amplify their business’s strengths, such as improving customer experiences, streamlining operations, and driving efficiency, without losing focus on what makes them beloved by customers. 

One of our customers, a tour bus operator known for exceptional customer service, faced a similar crossroads – how to grow without sacrificing the personal touch that they were known for. By introducing AI to handle routine tasks, the company freed up service agents to take on sales roles, shifting their service center from a cost center into a profit center. Revenue from the service team now exceeds its total running costs.

Uncomplicate to scale   

“Uncomplicate” is a powerful word. For me, it means rejecting complexity. In racing and leadership, it often sneaks in disguised as preparation — a new tool here, a new idea there — until we realize we’re making things much harder for ourselves. I’ve learned that firsthand, both in the boardroom and on the bike. 

It’s easy to overcomplicate triathlon logistics, especially when it comes to the bike. One year, I decided to upgrade to higher-tech inner tubes for my tires to increase my speed. But the first time I tested the new tubes during a training ride, one blew out, resulting in a flat tire. It was a humbling reminder that the shiniest tools don’t guarantee success. In fact, they often slow us down.

I’ve seen the same mistake in AI investment. Leaders go for the big-name software with bold promises, only to face long implementations, steep learning curves, and features that don’t match how teams actually work. Inside organizations, that software complexity compounds into fragmented systems, siloed teams, and deflated morale from tools that slow them down instead of helping them succeed. 

To truly scale with AI, leaders must remove complexity. This means choosing platforms that fit the organization, adopting tools thoughtfully with clear goals, and investing in people as much as technology so teams can use AI confidently. This approach to uncomplication makes space for clarity, speed, and growth.

Consistency over chaos 
While uncomplicating is about clarity of design, consistency is about discipline of execution.

When I’m training, there are plenty of mornings when snoozing my alarm sounds much more appealing than jumping in the pool or getting out for a long run. But success in endurance sports – and this AI race – comes from showing up every day with relentless effort and focus.

That same mindset is especially important for leaders seeking ROI from their AI investments. In a time where there’s a new AI company on the block almost every day, it’s easy to get distracted. Consistency means staying the course. Once you identify the right platforms and use cases that align with your strategy, commit to them. Set clear goals and integrate AI into daily workflows. Measure, refine, and repeat. It takes time, but the results will come.

Over a year ago, our sales team identified prospecting as the biggest bottleneck in its daily workflows. Before AI, nearly three-quarters of the process – from identifying target companies to researching contacts and writing personalized emails – was manual and time-consuming. The team wanted to spend less time on busywork and more time connecting directly with customers. By introducing automation and fine tuning over time, the team achieved 10x ROI in just three months.

It’s easy to confuse motion for momentum. But the companies that actually win the long game will focus on outcomes, align teams around shared priorities, and hold steady when everyone else chases the next big thing. Just like in Ironman training, progress doesn’t come from one heroic effort, but from a hundred consistent ones.

 
The long game of AI
Unlike an Ironman, AI doesn’t have a finish line. The AI race is long, unpredictable, and constantly changing. There really isn’t a roadmap – only the discipline to play to your strengths, uncomplicate your path, and keep showing up every day.

The leaders who learn to embrace this uncertainty will be the ones who make their organizations faster, more innovative, and more resilient. Tomorrow, pick one process, one team, or one customer interaction to uncomplicate with AI and start there. 

Progress comes from asking the right questions, showing up consistently, and having the patience and courage to keep learning as the course evolves.

In both racing and business, success comes when you stay your own course. Over time, this is how you build endurance and win the long game.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.



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SpaceX to offer insider shares at record-setting $800 billion valuation

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SpaceX is preparing to sell insider shares in a transaction that would value Elon Musk’s rocket and satellite maker at as much as $800 billion, people familiar with the matter said, reclaiming the title of the world’s most valuable private company. 

The details, discussed by SpaceX’s board of directors on Thursday at its Starbase hub in Texas, could change based on interest from insider sellers and buyers or other factors, said some of the people, who asked not to be identified as the information isn’t public. SpaceX is also exploring a possible initial public offering as soon as late next year, one of the people said. 

Another person briefed on the matter said that the price under discussion for the sale of some employees and investors’ shares is higher than $400 apiece, which would value SpaceX at between $750 billion and $800 billion. The company wouldn’t raise any funds though this planned sale, though a successful offering at such levels would catapult it past the record of $500 billion valuation achieved by OpenAI in October.

Elon Musk on Saturday denied that SpaceX is raising money at a $800 billion valuation without addressing Bloomberg’s reporting on the planned offering of insiders’ shares. 

“SpaceX has been cash flow positive for many years and does periodic stock buybacks twice a year to provide liquidity for employees and investors,” Musk said in a post on his social media platform X. 

The share sale price under discussion would be a substantial increase from the $212 a share set in July, when the company raised money and sold shares at a valuation of $400 billion. The Wall Street Journal and Financial Times earlier reported the $800 billion valuation target.

News of SpaceX’s valuation sent shares of EchoStar Corp., a satellite TV and wireless company, up as much as 18%. Last month, EchoStar had agreed to sell spectrum licenses to SpaceX for $2.6 billion, adding to an earlier agreement to sell about $17 billion in wireless spectrum to Musk’s company.

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The world’s most prolific rocket launcher, SpaceX dominates the space industry with its Falcon 9 rocket that lifts satellites and people to orbit.

SpaceX is also the industry leader in providing internet services from low-Earth orbit through Starlink, a system of more than 9,000 satellites that is far ahead of competitors including Amazon.com Inc.’s Amazon Leo.

Elite Group

SpaceX is among an elite group of companies that have the ability to raise funds at $100 billion-plus valuations while delaying or denying they have any plan to go public. 

An IPO of the company at an $800 billion value would vault SpaceX into another rarefied group — the 20 largest public companies, a few notches below Musk’s Tesla Inc. 

If SpaceX sold 5% of the company at that valuation, it would have to sell $40 billion of stock — making it the biggest IPO of all time, well above Saudi Aramco’s $29 billion listing in 2019. The firm sold just 1.5% of the company in that offering, a much smaller slice than the majority of publicly traded firms make available.

A listing would also subject SpaceX to the volatility of being a public company, versus private firms whose valuations are closely guarded secrets. Space and defense company IPOs have had a mixed reception in 2025. Karman Holdings Inc.’s stock has nearly tripled since its debut, while Firefly Aerospace Inc. and Voyager Technologies Inc. have plunged by double-digit percentages since their debuts.

SpaceX executives have repeatedly floated the idea of spinning off SpaceX’s Starlink business into a separate, publicly traded company — a concept President Gwynne Shotwell first suggested in 2020. 

However, Musk cast doubt on the prospect publicly over the years and Chief Financial Officer Bret Johnsen said in 2024 that a Starlink IPO would be something that would take place more likely “in the years to come.”

The Information, citing people familiar with the discussions, separately reported on Friday that SpaceX has told investors and financial institution representatives that it’s aiming for an IPO of the entire company in the second half of next year.

Read More: How to Buy SpaceX: A Guide for the Eager, Pre-IPO

A so-called tender or secondary offering, through which employees and some early shareholders can sell shares, provides investors in closely held companies such as SpaceX a way to generate liquidity.

SpaceX is working to develop its new Starship vehicle, advertised as the most powerful rocket ever developed to loft huge numbers of Starlink satellites as well as carry cargo and people to moon and, eventually, Mars.



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National Park Service drops free admission on MLK Day and Juneteenth while adding Trump’s birthday

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The National Park Service will offer free admission to U.S. residents on President Donald Trump’s birthday next year — which also happens to be Flag Day — but is eliminating the benefit for Martin Luther King Jr. Day and Juneteenth.

The new list of free admission days for Americans is the latest example of the Trump administration downplaying America’s civil rights history while also promoting the president’s image, name and legacy.

Last year, the list of free days included Martin Luther King Jr Day and Juneteenth — which is June 19 — but not June 14, Trump’s birthday.

The new free-admission policy takes effect Jan. 1 and was one of several changes announced by the Park Service late last month, including higher admission fees for international visitors.

The other days of free park admission in 2026 are Presidents Day, Memorial Day, Independence Day, Constitution Day, Veterans Day, President Theodore Roosevelt’s birthday (Oct. 27) and the anniversary of the creation of the Park Service (Aug. 25).

Eliminating Martin Luther King Jr. Day and Juneteenth, which commemorates the day in 1865 when the last enslaved Americans were emancipated, removes two of the nation’s most prominent civil rights holidays.

Some civil rights leaders voiced opposition to the change after news about it began spreading over the weekend.

“The raw & rank racism here stinks to high heaven,” Harvard Kennedy School professor Cornell William Brooks, a former president of the NAACP, wrote on social media about the new policy.

Kristen Brengel, a spokesperson for the National Parks Conservation Association, said that while presidential administrations have tweaked the free days in the past, the elimination of Martin Luther King Jr. Day is particularly concerning. For one, the day has become a popular day of service for community groups that use the free day to perform volunteer projects at parks.

That will now be much more expensive, said Brengel, whose organization is a nonprofit that advocates for the park system.

“Not only does it recognize an American hero, it’s also a day when people go into parks to clean them up,” Brengel said. “Martin Luther King Jr. deserves a day of recognition … For some reason, Black history has repeatedly been targeted by this administration, and it shouldn’t be.”

Some Democratic lawmakers also weighed in to object to the new policy.

“The President didn’t just add his own birthday to the list, he removed both of these holidays that mark Black Americans’ struggle for civil rights and freedom,” said Democratic Sen. Catherine Cortez Masto of Nevada. “Our country deserves better.”

A spokesperson for the National Park Service did not immediately respond to questions on Saturday seeking information about the reasons behind the changes.

Since taking office, Trump has sought to eliminate programs seen as promoting diversity across the federal government, actions that have erased or downplayed America’s history of racism as well as the civil rights victories of Black Americans.

Self-promotion is an old habit of the president’s and one he has continued in his second term. He unsuccessfully put himself forwardfor the Nobel Peace Prize, renamed the U.S. Institute of Peace after himself, sought to put his name on the planned NFL stadium in the nation’s capital and had a new children’s savings program named after him.

Some Republican lawmakers have suggested putting his visage on Mount Rushmore and the $100 bill.



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JPMorgan CEO Jamie Dimon says Europe has a ‘real problem’

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JPMorgan Chase & Co. Chief Executive Officer Jamie Dimon called out slow bureaucracy in Europe in a warning that a “weak” continent poses a major economic risk to the US.

“Europe has a real problem,” Dimon said Saturday at the Reagan National Defense Forum. “They do some wonderful things on their safety nets. But they’ve driven business out, they’ve driven investment out, they’ve driven innovation out. It’s kind of coming back.”

While he praised some European leaders who he said were aware of the issues, he cautioned politics is “really hard.” 

Dimon, leader of the biggest US bank, has long said that the risk of a fragmented Europe is among the major challenges facing the world. In his letter to shareholders released earlier this year, he said that Europe has “some serious issues to fix.”

On Saturday, he praised the creation of the euro and Europe’s push for peace. But he warned that a reduction in military efforts and challenges trying to reach agreement within the European Union are threatening the continent.

“If they fragment, then you can say that America first will not be around anymore,” Dimon said. “It will hurt us more than anybody else because they are a major ally in every single way, including common values, which are really important.”

He said the US should help.

“We need a long-term strategy to help them become strong,” Dimon said. “A weak Europe is bad for us.”

The administration of President Donald Trump issued a new national security strategy that directed US interests toward the Western Hemisphere and protection of the homeland while dismissing Europe as a continent headed toward “civilizational erasure.”

Read More: Trump’s National Security Strategy Veers Inward in Telling Shift

JPMorgan has been ramping up its push to spur more investments in the national defense sector. In October, the bank announced that it would funnel $1.5 trillion into industries that bolster US economic security and resiliency over the next 10 years — as much as $500 billion more than what it would’ve provided anyway. 

Dimon said in the statement that it’s “painfully clear that the United States has allowed itself to become too reliant on unreliable sources of critical minerals, products and manufacturing.”

Investment banker Jay Horine oversees the effort, which Dimon called “100% commercial.” It will focus on four areas: supply chain and advanced manufacturing; defense and aerospace; energy independence and resilience; and frontier and strategic technologies. 

The bank will also invest as much as $10 billion of its own capital to help certain companies expand, innovate or accelerate strategic manufacturing.

Separately on Saturday, Dimon praised Trump for finding ways to roll back bureaucracy in the government.

“There is no question that this administration is trying to bring an axe to some of the bureaucracy that held back America,” Dimon said. “That is a good thing and we can do it and still keep the world safe, for safe food and safe banks and all the stuff like that.”



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