Your overhead runs twelve months a year. Your revenue runs six to nine. Stephen has run two seasonal businesses — an exterior home maintenance company where the phone stopped the day the trees went bare, and a roll-off dumpster company tied to roofers who shut down in November. This episode walks both of them: what…
Thirty minutes into a conversation with a business owner, we usually know. Not from the financials — from the way the owner answers. Christian and Stephen each walk through their top five red flags: the specific things that make an advisor quietly reclassify a business from healthy to fragile. After each one, the other host…
Most business advice gets repeated until nobody checks whether it’s still true. Today we check. Christian and Stephen put eight pieces of conventional wisdom on the table and argue them out. Revenue is the most overrated number in business. You should think about your exit from day one. Hire slow, fire fast. Your bank is…
We talk about capital deployment, deal structure, and business strategy every episode. Today we’re putting our money where our mouth is. Christian and Stephen each walk through exactly where they’d deploy $1 million into a business right now. Where does the first dollar go? What would they never do with it? And what’s the highest-leverage…
Imagine you just won the biggest contract your company has ever seen. Your team can handle it. Your reputation earned it. And you’re about to run out of money — not because anything went wrong, but because the cash goes out on Day 1 and the client doesn’t pay until Day 90. That 90-day gap…
This week, Nvidia helped its customers finance $500 billion in AI infrastructure. The Los Angeles Lakers sold for a record $12.5 billion. And Berkshire Hathaway deployed $39 billion after sitting on nearly $400 billion in cash for years. Most people treat those as rich-company stories. This episode treats them as operator playbooks. In this solo…
Private equity firms are paying 4x earnings for individual businesses in fragmented markets — then selling the combined platform for 10x. Same businesses. No magic. Just scale. But here’s what most operators miss: you don’t need a PE firm to run this play. You can do it yourself — with your existing business as the…
Mailchimp raised zero dollars in outside capital. Zero. And sold for twelve billion. WeWork raised twenty-two billion dollars. And filed for bankruptcy. Both companies were growing. Both had revenue. The difference wasn’t the product, the market, or the timing. It was readiness. Capital amplifies what’s already working — or funds what’s already broken for longer….
If you think your business is in great shape right now — this episode is specifically for you. Blockbuster had 9,000 stores, 65 million registered customers, and a market position no one thought was vulnerable. They also had $800 million in annual revenue tied to a pricing model built on customer frustration. When Netflix removed…
You negotiate for months to land a $3 million purchase price. Then the deal closes and after debt payoff, taxes, transaction fees, escrow holdbacks, and earnout risk, you walk away with significantly less than you expected. Most business owners don’t know this is coming until they’re already sitting across from a buyer. And by then,…