Issue 24: From 2016 to this.

It has been a few months. In my defense, we have been busy building. 90%+ of fundraising is smoke and mirrors. We built the line that cuts through it. Our new flagship goes live at dealbox.io next week.

Here is the thesis.

Fundraising is the founder's curse. Great products die in obscurity every day simply because the founder could not secure investors. The cynical take is that founders who cannot fundraise should not be funded. We disagree. Some of the best founders we have ever met are technical, live outside the major hubs, and are building something real. They just need a wingman.

Worse, it turns into a full-time job at exactly the moment you cannot afford one. Sheets, Drive, DocSend if the budget stretches. Decks sent on a wish and a prayer. No idea who opened the file, how long they sat in the data room, when they last looked, or where they rank against everyone else circling the deal. When someone is finally ready, you are scrambling at midnight in DocuSign with a redline you should have seen Tuesday.

We built the thing that gives you that time back. Upload your deck. Thirty seconds later you have a live portal, an intelligent data room, a shareable link, and a funnel that actually behaves like a funnel.

We are calling it Investor Onboarding, and it has been in the making since we launched Deal Box ten years ago this coming September. If you are an issuer client, the paid portal is yours free for nine months. But it gets better. Every issuer we package also gets listed on our redesigned 506(c) platform at platform.dealbox.io (this will continue to be a Title II matchmaking platform under the JOBS Act Section 201(c) exemption, with zero transaction fees; we are not a broker-dealer).

We earn on technology and advisory services provided to issuers only.

The US minted over 562,000 new millionaires in 2024. Demand for fee-free access to alternatives has never been higher. We want this to be the place angels start. Reply to this email for early access.

The beta is live with a small group of friends and clients. If you have ever raised a round or allocated to one, this is the thing.

Five things this week. Plus a personal note from Oahu at the end.

Quick note before we dive in: we switched newsletter providers. Going forward, the Dispatch lands every Friday from thomas@dispatch.dealbox.io instead of thomas@dealbox.io. Same Thomas, same newsletter, new sender. Add it to your contacts so we do not end up in spam.

The CAPE Yield Just Flashed 1999

IMAGE: Shiller Excess CAPE Yield chart

Take the S&P earnings yield. Subtract the 10-year Treasury, currently 4.3 percent. What is left is Shiller's excess CAPE yield. Cleanest single read on what equities will do over the next decade.

It just hit its worst level in over a hundred years.

The lesson from 1999 was not "stocks are bad." The lesson was that public markets and private markets do not move on the same clock. When public valuations get this stretched, private capital becomes more expensive, more selective, and more punitive on terms.

For founders raising right now. Pick your investors carefully. Do not let scarcity push you into a deal that costs you the company on the back end.

What "Standard" Platform Fees Actually Cost You

"Two percent platform fee, twenty percent carry."

Eyes glaze over. Sign the doc. Move on.

We ran the numbers on what that line item actually subtracts at a $100M exit, compared with raising the same capital direct from accredited angels through a portal you control. The gap is not a rounding error. It is a house. In some cases, two houses.

The fees are not the problem. The opacity is. Most founders never see the dollar version of the percentage they signed.

Read the breakdown: The Real Cost of Platform Fees.

506(b) or 506(c). Pick Wrong, Pay Forever.

Every founder we onboard asks the same question in week one. Which exemption.

506(b) lets you raise from people you already know. No general solicitation. Self-attested accreditation is fine.

506(c) lets you market the raise publicly. Every investor must be verified accredited. No exceptions.

You cannot start one and switch to the other halfway through without consequences. Pick wrong and you are either leaving qualified leads on the table or quietly stepping into securities trouble.

Plain-English explainer: 506(b) vs 506(c): How to Choose.

The Fundraising Process, Step by Step

Most founders raise the same way. Pitch deck. Cold list. Coffee meeting. Hope.

The data on outcomes from that approach is brutal. Less than 1 percent of seed-stage companies that fundraise the traditional way close a round in their target window.

We mapped the process differently. Week 2, you have a real model. Week 6, your portal is live. By week 10, you know which investors are actually engaging and which ones are ghosting. Same time, better signal, fewer surprises.

Read it: The Deal Box Fundraising Process.

This Week's Costliest Encore

Red Lobster just brought back Endless Shrimp. The exact promotion that lost $11 million in a single quarter and pushed it into Chapter 11 under previous ownership.

The thing that nearly killed them was not the debt, not the closures, not the customers camping at tables for hours. It was making a loss-leader permanent because it moved traffic.

There is a lesson in there for anyone running a business right now. Your incentive structure is your Endless Shrimp. Reward short-term volume too aggressively and the unit economics you ignored decide whether you exist next quarter.

Also, RIP to the only chain that lost money faster the more customers it served.

A Note From Oahu

The windward side took a beating these past few weeks. Historic flooding. Roads gone. Families displaced. The kind of weather that reminds you which surf you should not paddle out into.

Thankfully we are fine. Our neighbors are not all fine. A few clients in the islands have been dealing with cleanup more than markets, and that is the right call.

If you have the bandwidth, the Hawai'i Community Foundation and the American Red Cross Pacific Islands are moving real resources to families that need them. No ask beyond that. Macro charts are one kind of weather. There are other kinds that matter more.

One last thing.

If you know a founder raising a seed or Series A who deserves better than the VC grind, forward this. Reply with their name. If they launch a portal with us, I will send you a thank-you you will actually want.

And if you want to see what we have been building for the last two months, go to dealbox.io and click Get Started. Beta is open this week to friends of the business. Pull up. Show me what is broken. We will fix it.

Thomas Carter
Founder and CEO
Deal Box

April 17, 2026 · Oahu