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Continue reading →: What Is an Earn-Out? A 2026 Guide for Business SellersEarn-outs pay out roughly 21 cents on the dollar, which makes the contingent slice of your purchase price the part that deserves the most scrutiny. As someone who has sold a company and read a lot of letters of intent since, I stopped reading the headline number first. The number…
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Continue reading →: SEP IRA vs. Solo 401(k): The 2026 Small Business GuideOne of these plans can shelter up to $72,000 of your income this year and picking the wrong one can leave five figures on the table. I have owned businesses on both sides of this decision: one I scaled with a full team and eventually sold, and another I still…
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Continue reading →: Buying and Selling a Car: 2026 Tax and Credit RulesThe IRS, your state, and the credit bureaus all take a position on every vehicle transaction, and the rules changed enough for 2026 that the sticker price is the least interesting number on the deal. I once sold a street-legal golf cart and still had to grind through Ohio’s title…
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Continue reading →: How to Value a Small Business: Multiples That Matter in 2026SDE, EBITDA, and realistic multiples by industry, plus the playbooks sellers and buyers use to move the final number. The first time an acquirer walked me through their model for my last business, half of the price hinged on what happened after the sale. That lesson explains why two nearly…
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Continue reading →: The Online Sales Conversion Funnel: A 2026 Owner’s GuideMaster the metrics, the math, and the levers that turn ad spend into profit at every stage of your funnel. I co-founded Cloud Water Filters, a D2C smart-home water filtration company, so I live inside this exact funnel every week: paid traffic in one end, contribution margin out the other,…
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Continue reading →: Dot-Com Bubble vs AI Bubble: How 2026 Compares to 2000I’m not trying to sound the alarm bells for the sake of clicks, but the patterns I’m seeing between the dot-com bubble and potential AI bubble are too eerily similar to ignore. If you read tech and financial news and watch podcasts like me, you no doubt are hearing similar…
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Continue reading →: Mark Cuban Is Right: Employee Equity Pays Off in 2026Cuban wants every founder to give stock to every employee, and the math, the culture, and his own track record all say he is onto something. After being involved with dozens of startups, I can tell you the employee option pool on a cap table reveals more about a founder…
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Continue reading →: Small Business Profit Margins by Industry: 2026 BenchmarksYour industry sets your margin ceiling before you ever sell a thing; here is where that ceiling sits for 12+ business models. I’ve owned both ends of this table: an insurance marketplace that threw off software-style margins and a D2C water filtration company that fights for every point after freight…
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Continue reading →: The Bigger Your Company Gets, the Harder It Is to SellThe M&A data is blunt: deal volume lives at the bottom of the market, buyers vanish at the top, and size quietly destroys your exit options. In 2024, roughly 95% of all M&A transactions were valued under $1 billion, and the lower middle market alone accounts for an estimated 70%…
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Continue reading →: Prediction Markets 2026: How Sharps Turn Movies Into MoneyTraders are pulling six figures out of Rotten Tomatoes scores, award shows, and Fed meetings. Here is how the edge actually works, and what founders and angel investors can steal from it. I have made dozens of investments, and every one of them is a bet on a probability I…
