Welcome - and thanks for being here.
I started The Deal Office because I kept seeing the same thing happening across numerous deals. Founders coming to market with real businesses and real opportunities and losing deals to problems that were completely fixable. Confusing structure. Cap table issues. Financial presentation that focused on the wrong things to the exact people they needed to impress.
It was very rarely a bad business. No one caught the problems before they went to market.
I've spent over a decade working on lower middle market deals - raises, acquisitions, credit facilities, restructurings. Mostly on transactions between $500K and $10M. The kind of deals that don't make headlines but represent most of what actually happens in the private market. The pattern I kept seeing was that most founders had never sat on the other side of the table. They had no idea what the investor, acquirer, or lender was actually looking at.
Closing Deals was created to fill that gap.
What we cover
Every week we publish one idea, one pattern, or one insight from the investor's, acquirer's, or creditor's side of the table. Not general business advice. Not motivational content. The actual view from the other side - what's being evaluated, what's creating hesitation, and what makes a deal move or stall out.
The content covers the full deal spectrum: capital raises most weeks, with M&A, restructuring, and governance mixed in. The decisions founders make at each stage are connected, and understanding the whole picture makes you better at navigating any part of it.
Some issues will make you feel more prepared. Some may strike a nerve about something you hadn't considered. Both are useful as you sharpen your skills or prep for a transaction.
What The Deal Office does
If something you read resonates we offer a next step.
The Deal Stress Test is a 48-hour written diagnostic of your deal, reviewed from an investor's perspective. It surfaces the gaps and structural issues before you're sitting across from an investor and finding out the hard way. Our team of experienced advisors helps you plug the gaps and bulletproof your package.
You'll hear more about it as we go. For now, just know it exists and what it's for.
What to expect
Issues arrive weekly. Short enough to read in under four minutes. One idea covered properly. Always written from the other side of the table.
If you know a founder who's raising - or is about to - forward this to them. They can subscribe here.
Good to have you with us.
Sarah
The Deal Office