Most owners know a transition is coming, but very few are actually ready. In one major study: 68% of owners had sought advice on a business transition. 78% still had no formal transition team. Only about 1 in 3 had a documented exit plan. That’s how otherwise good businesses can fail -- by not planning the handoff. 🍊

“A better-functioning ownership transition market could preserve jobs and local prosperity at scale. Effective transitions could keep up to 12 million jobs in place and protect about $250 billion in annual local spending power.” — McKinsey

The Produce Department is growing! We are looking for a part-time Social Media Manager. If you’re interested in joining us apply below: orangejuice.com/pages/hiring…

If only there was a… refreshing alternative. ORANGE JUICE. So sweet. 🍊

Do you subscribe to the ORANGE JUICE blog? orangejuice.com/blogs/insigh… Always fresh pressed. 🍊

Most founders say they care about “legacy.” Almost none of them have defined what that actually means. Harvard Business School recommends starting with five groups: Yourself. Your family. Your employees. Your customers & partners. Society. Only after you prioritize what matters for each should you decide what happens to the company. Define → Explore → Experiment → Execute. Full article from HBS: hbr.org/2025/09/the-founders…

How it actually works when a business is part of ORANGE JUICE The operating company continues to run largely as it did before. Management stays in place and keeps day-to-day control. The brand, name, and customer relationships remain intact. Culture is preserved. What changes is the ownership and support structure: Permanent capital — no fund-life pressure to sell Access to shared resources, network, and operational tools Practical AI support from our in-house experts Performance-aligned incentives for management (in the spirit of the Berkshire model) Optional strategic advice without forced interference Founders can stay as involved as they want. If they later choose to step back, the structure is designed for continuity. Built for long-term compounding, not short-term extraction. 🍊

McKinsey calls it the “Great Ownership Transfer.” Harvard calls it the “Silver Tsunami.” Business Matters calls it “The Great Handover.” Either way, millions of American businesses are about to change hands. Whatever the name is, we’re here for it. 🍊

Building a business takes decades. Founders deserve more than one path when it’s time to transition ownership 🍊

The “Great Ownership Transfer” is underway. By 2035, roughly 6 million small and midsize businesses in the United States will face an ownership transition as baby-boomer owners retire. More than 1 million of those firms are viable candidates for continued ownership or sale. Representing up to $5 trillion in enterprise value. Supporting tens of millions of jobs across the country. This is the largest wave of small-business ownership transitions in modern American history. Millions of companies that employ tens of millions of workers will either change hands or shut down over the next decade. How this wave is handled will shape jobs, local prosperity, and economic mobility for decades to come 🍊 Full McKinsey report: mckinsey.com/institute-for-e…

Small & medium businesses are the backbone of the U.S. economy. Did you know that: There are 36.2 million small businesses — 99.9% of all businesses in the country. They employ 62.3 million people — 45.9% of the private-sector workforce. SMBs generate 43.5% of GDP and 35% of private-sector receipts. Small businesses have created the large majority of net new jobs over the past few decades. 61% of all net new jobs since 1995. 20.7 million net new jobs vs. 13.2 million from large businesses. In many recent periods they have accounted for 80–90% of net job growth. The local impact is even stronger: money spent at small businesses recirculates more in the community than spending at large chains. And for millions of Americans, starting or owning a business remains one of the most powerful and accessible pathways to economic mobility — building wealth, independence, and opportunity. It's important to protect that pathway 🍊 Sources & learn more: advocacy.sba.gov/2026/02/03/…

Found out more and apply here: orangejuice.com/pages/invest…

We’re hiring! ORANGE JUICE is looking for a high-agency Investment Associate who wants more than a traditional seat. High ownership from day one. Direct input into investment decisions. If this sounds like you, see link below to learn more and apply! 🍊🔥

"Free-market productivity pushes prices down. A credit-based system requires perpetual inflation just to survive. One system rewards building. The other rewards debasing." — @JeffBooth Full piece from Jeff here: jeffbooth.ca/articles/the-ca…

(3/3) The AI adoption gap is less about access to tools and more about the expertise, bandwidth, and process changes needed to embed AI into actual workflows. ORANGE JUICE is building a world-class in-house team to support practical AI adoption across the portfolio. Individual businesses shouldn't have to figure it out alone! 🍊

(2/3) The jump from “using AI” to real revenue or cost improvements is still hard. Many get time savings on drafting content or summarizing meetings. Far fewer successfully turn those gains into measurable improvements in revenue or operating costs. Larger companies are much more likely to report meaningful financial impact.

(1/3) Around 58% of U.S. small businesses now report using generative AI — up from roughly 23% a few years ago. That sounds high, but many smaller firms still use little or none. Even among those who do, most remain in early experimental stages. Skills gaps remain one of the top barriers, cited by roughly one in three SMBs.

Founder and management alignment is built into the model. Founders receive part of the purchase price in ORANGE JUICE equity, so they continue to participate in the long-term growth of the whole group. At the same time, local management keeps meaningful incentives tied to the performance of their own business. When they operate it well, they benefit — similar to the approach long used by companies like Berkshire Hathaway. We want the people closest to the work to stay motivated and aligned for the long term. 🍊

(3/3) Same pattern with Toys “R” Us. A $6.6B LBO in 2005 loaded the company with more than $5B in debt. When Amazon, Walmart, and Target intensified competition, the debt left almost no room to invest and adapt. It filed for bankruptcy in 2017. Again: the market shift was the catalyst. The leverage is what made it fatal. 🍊

(2/3) Things can go badly wrong when a business is over-levered. Energy Future Holdings was the largest LBO in history — a $45B deal in 2007 that loaded it with ~$40B in debt. If everything had gone as planned, it might have been fine. But does that ever actually happen? When the shale gas revolution crashed energy prices, the debt left almost no room to adapt. It filed for bankruptcy in 2014. The market shift was the catalyst. The leverage is what made it fatal. 🍊