To the chorus of a thousand clinking name badges, we sat down last week to the ISMWorld 2025 keynote speaker: Kevin O’Leary. “Mr. Wonderful.” His insights and thoughts over the next hour or so were fascinating, thought-provoking, and edged into thoughtful criticism of both political parties. At the end of the next day, the closing keynote provided a gentle counterpoint from Gina Raimondo, formerly the Secretary of Commerce and governor of Rhode Island. Their insights on tariffs, the #1 export of the United States, the best negotiation tool, living life, policy, and advice to allies of the United States were fascinating, riveting, and thought-provoking. Today I’ll share my notes from these keynotes for both those who were in attendance in Orlando and those who were unable to join.
Kevin O’Leary
Kevin O’Leary is best known as one of the “sharks” on the TV show Shark Tank, and is primarily an investor at this point in his life. He also stays engaged with U.S. politics, as he knows his notoriety and wealth can open doors closed to others. He advocates most strongly for businesses with 5-500 employees because they account for 62% of U.S. job creation.
Trump and Tariffs
Mr. O’Leary talked about the current tariff market as correcting a long-standing trade imbalance between the U.S. and its partners. He noted even friendly trade partners have had an imbalance not previously corrected by leaders of either U.S. political party. Mr. O’Leary’s prediction is that we will end up with a 10% reciprocal tariff from all countries except China, in echo to the European VAT tax. He thinks this will settle at that point just before the midterm elections in November 2026, so the supply chain professionals have to ride this tariff wave as best we can for the next 14-18 months. He does think many things will come back to the U.S., but some items (like domestic aluminum) would take 15-20 years to be made in the States. He never did get as specific about China and seemed more bullish on moving manufacturing to “friendlier” countries.
He spoke a bit about President Trump and how he interacts with others. Mr. O’Leary said a lot of policy gets written in Mar-a-Lago on Saturday and Sunday, then brought back to the White House on Monday. He talked about the “noise to signal” ratio in communication, where President Trump tends to create more noise than actual signal when he speaks. The trick is to hear through all of the noise and get to the signal. In contrast, Elon Musk is all signal with no noise, which is why he is so socially awkward.
Investments
Mr. O’Leary noted that even though he has investments in several dozen companies at any given time, he tries not to have more than 5% in any one stock, bond, or company except for real estate. Real estate is currently about 30% of his portfolio. He said the investment that succeeds is never the one he thinks will succeed, and karma and luck have a big impact on company success. He commented many of his best investments were companies run by women because he finds women to be particularly good at risk mitigation (definitely a key part of running a supply chain!).
Mr. O’Leary noted that the #1 export of the United States is the American Dream. Shark Tank is an ambassador to that dream, and the primary job of any U.S. President is to not kill the American Dream. To this end, he is strongly opposed to the recent policy to not allow foreign-born students at Harvard University and instead believes we should fast-track those students to citizenship. Research drives the U.S. competitive advantage, so it’s something we have to focus on and use to stay ahead.
Because I don’t have anywhere better to put it, Mr. O’Leary also noted that the best negotiation tool is silence. This reminded me of a clip from the tv show 30 Rock where someone uses silence to negotiate with the character Jack Donaghy, who then uses it in his own negotiation. YouTube clip here. I will say I personally struggle with this one as I am a person who doesn’t sit well with silence. I’ll keep working on it!
Living Life
Kevin O’Leary recommended Keith Richards’ autobiography “Life” as a source of his own motivation (I’ll have to pick up a copy or download an audiobook!). Mr. O’Leary tells his family to pick a city every weekend to be in and then uses his wealth to fly himself and his family there. He believes in living the life he’s earned. He also noted that Steve Jobs was always hyper-focused on the 3-5 tasks he needed to do every day. Not the strategic or long-term outlook, but just the 3-5 things daily. This resonated with my fabulous career coach’s daily journal prompt: 3 things you’re grateful for, 3 wins, and 3 intentions for the next day.
Full disclosure: I am terrible at journaling. But the universe keeps yelling at me to do it, so I’m redoubling my efforts. You can help remind me and keep me accountable.
Mr. O’Leary also commented that success comes from living some portion of your day outside your comfort zone. Humans need balance, and he gave the example of a CFO he knows who still regularly does classical dance. Mr. O’Leary loves wine and playing guitar, so he recommended the documentary Steely Dan: The Making of Aja for those interested. As for myself, I quilt as my balance. Below is one of my recently finished quilts, this pattern is modified slightly from one called Triple Treat and was designed by a wonderful quilt designer named Bonnie Hunter.
Gina Raimondo
The closing speaker for ISM World was the intelligent and thoughtful Gina Raimondo, who was the Secretary of Commerce from 2021 to 2025 and the governor of Rhode Island from 2015 to 2021. Before entering politics, she co-founded Rhode Island’s first venture capital firm and is very pro-business. She shared some thoughts on trade policy and advice to U.S. trade allies.
Trade Policy
Secretary Raimondo was a big advocate of the CHIPS and Science Act signed into law in 2022 and mentioned it multiple times. In 2021, 100% of all semiconductor chips in the U.S. were made in Taiwan and 95% were tested and packaged in China. She noted the current tariff approach was like “carpet bombing,” but didn’t offer as specific predictions or thoughts as Mr. O’Leary.
Ms. Raimondo repeatedly noted that the average senator doesn’t truly understand how the tariff affects businesses in their state and encouraged companies to tell their story with their representatives. She also noted that the U.S. needs to make friends with our largest allies, especially in Asia. She specifically cited Indonesia, the Philippines, India, and Malaysia. She noted that this current U.S. administration does engage with companies and constituents, so it is worth engaging with the government to tell your story. She also noted that board rooms don’t truly understand supply chains (this is an argument to get more supply chain leaders on company boards!) and that not everything can be made in the U.S.
Leadership
From a personal philosophy, Gina Raimondo noted that leaders have to care more about the people they serve than themselves. Secretary Raimondo has mentioned recently that she would consider a Presidential run, and after watching her speak I can see it. She was articulate, more center-left in political stance, and has a deeper understanding of the business world than most politicians. She may be one to watch a little closer as the 2028 U.S. presidential election looms.
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My book, Transform Procurement: The Value of E-auctions is now available in ebook and paperback formats: https://www.amazon.com/dp/B0F79T6F25
