Pierce Leonard (@LeonardPierce) header
Pierce Leonard (@LeonardPierce) profile picture

Any risk, any size. D&O, E&O, cyber, GL, comp for funds, fintech, robotics, space, Main Street. AI-powered brokerage. Director, Specialty Programs @ Equal Parts

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Joined February 2010
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Any risk, any size. That's the job. Funds, fintech, robotics, space, the restaurant down the street. If it's a real business, I'd love to help.
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Board minutes are an insurance document. In a derivative suit, the record of what the board reviewed and when decides whether the conduct exclusion bites. Sloppy minutes are free evidence for the plaintiff. Write them like the carrier will read them.
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Domestic D&O forms are mostly silent on digital assets. Silence is not coverage. Bermuda forms define the asset, the custody standard, and what triggers a loss. Ask to see the definition page, not the marketing summary.
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Fair value accounting now pushes Bitcoin swings straight through earnings. A 30% quarter is not a footnote, it is a reported loss. Expect securities claims to follow the earnings line, and check that your D&O covers disclosure, not just theft.
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Carriers are adding a human in the loop condition to AI policies. If your product lets the agent act without review, that condition is breached and the claim is declined. Automation is a coverage decision, not just a product decision.
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A vendor used Westlaw headnotes to write ROSS Intelligence's AI training memos. On Sept 29 the Third Circuit held ROSS's use of 2,243 headnotes was not fair use. ROSS did not contest that the vendor's copying was attributable to it. Ask your data vendor where its data came from.
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Whoa. The SEC says BG Wealth Sharing and DSJ Exchange showed investors false SEC filings, including a Form D, as proof the SEC had approved them. A Form D is a notice, not an approval, the complaint says. It alleges $130M+ raised. If you file one, never write "SEC approved."
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Reg A+ Tier 1 caps you at $20M and still sends you through state blue sky review, one state at a time. Tier 2 caps at $75M and preempts that review. Founders pick Tier 2 for the bigger cap and miss the bigger reason.
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Two lawsuits, one from investors and one from the board, can count as one claim if they share a common fact pattern. That is the interrelated wrongful acts clause. One limit, one retention, not two. Read that definition before you assume you have two shots.
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The insurance industry's AI problem is not underwriting. It is that nobody can explain a declination to a founder in plain English. The first broker who does that owns the AI startup market.
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Listen to the @hornets on WSIC
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Pierce Leonard retweeted
rockin n rollin w these 5! #HiveMentality | @NovantHealth
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Bermuda D&O is not as offshore as founders assume. Policies are written in USD, governed by NY or Bermuda law, and defended by US counsel. What sits offshore is the capacity, not the claim. Ask who actually handles the claim.
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Pierce Leonard retweeted
Some entrepreneurs leave an impression because of what they build. Others because of how they live. Adam Robinson did both. Years ago, my friend David Carpentier introduced me to Adam, knowing we'd hit it off given my love for entrepreneurs and their stories and living his founder story for everyone to see. We first met at a bar on Lake #Austin at sunset, just after he'd gotten off the water (that was his style 100%). The next time on his boat surrounded by a group of founders he'd invited out for an evening of wake surfing and lake enjoyment with a little business talk. What was cool was how naturally he brought people together. Different personalities, different businesses, different backgrounds. With him was the place to be and the life you want to live. I later had the opportunity to produce a video project for Adam and Retention.com, where I saw firsthand his incredible creativity, energy, humility, and seemingly endless drive. What a wild ride was on. He was fearless about building in public, openly sharing his wins, losses, and lessons. He was also a passionate advocate for bootstrapping, shaped by his own entrepreneurial experiences. But what impressed me most wasn't his business success at @retentiondotcom . It was how generously he shared his time, knowledge, and connections. As part of his weekly outings, I suggested he invite a group of women entrepreneurs out on the lake to connect, since not many women own boats in Austin. It would be a unique way for female founders to connect. He loved the idea and happily made it happen. Got to meet his wife Helen and his dog on those gatherings and you could tell his family was of the same spirit At one point, there was a 1st time wake surfer trying to get up, so, without thinking, Adam jumped in the water to give her guidance and tips. A microcosm of his approach to helping others and life...just jump in and do it. One of those founders, Ingrid Sanders (the one in the water getting advice), captured it best. "I only met him that once, but he struck me as everything you’d want in a person and a beautiful family." Like so many others, I was heartbroken to hear about the tragic plane accident in Florida that took Adam and his family. I've read the outpouring of tributes. All echoing similar sentiments about who he was. Generous. Welcoming. Creative. Humble. Funny. Full of life. Adam built successful businesses, but his greatest legacy may be the people he brought together and the lives he touched along the way. He and his family lived a beautiful life, and he did it his way. Building, laughing, taking risks, enjoying every moment, and helping others do the same. His energy and spirit will be deeply missed, but judging by the countless stories being shared, one thing is certain...@RetentionAdam will not be forgotten. Rest in peace, my friend. #hangten
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Bitcoin treasury stocks trade at a premium to the coins they hold until they do not. When that premium collapses, shareholders sue over dilution and disclosure. Your D&O needs to respond to a valuation theory, not just a custody failure.
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You indemnified your customer for anything the model outputs. That promise is contractual liability, and your E&O likely excludes it. The policy pays for your negligent service, not for a warranty you signed. Read the MSA and the exclusion together.
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Reg A+ Tier 2 caps you at $75M and hands you thousands of non-accredited shareholders. That is a public company liability profile without a public company insurance budget. Most issuers learn that at the first demand letter.
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Your D&O application is a representation the carrier can rescind on. Check no litigation, and a founder's old dispute surfaces, and the policy can vanish back to day one. Read the application like a securities filing, because a plaintiff will.
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If your Bitcoin sits on an exchange, your board is relying on a counterparty balance sheet, not a custody arrangement. Ask for the trust charter, the SOC 2, and who holds signing authority. Then ask what D&O says about that decision.
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Your AI model changed three times since the carrier bound the policy. If the application described version 1 and the claim arises under version 3, underwriting can argue they priced a different risk. Version control is an insurance control now.
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Reg CF requires a Form C-U when you hit 50% and 100% of your target. Founders treat it as paperwork. Plaintiffs treat it as the record of what you told investors. File on time and make the numbers match the dashboard.
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