I was asking for too little.
In my second year raising capital for hotel conversions, we were trying to raise $2 million or $3 million at a time.
Then I'd go to family office conferences and hear a minimum check size of $20 million. Or $50 million. The lowest I remember hearing was $10 million.
My opportunity could be real and still be the wrong size for the person across the table.
That was an expensive thing to learn slowly.
There's a bad lesson you could take from that story: "Fine. I'll just ask for $50 million."
A bigger ask doesn't fix a small opportunity, a weak team or a business plan that doesn't hold up.
If I were going after a $50 million family office equity check today, these are the seven steps I'd work through.
Step 1: Line up your anchor operator.
You must have an anchor operator.
If you're the anchor operator, that probably means 10 or more full cycle deals behind you, deals you've taken from purchase to sale.
If you don't have 10 plus full cycle deals, then partnering with an anchor operator is very important. You find them by being active in your industry and building real relationships with groups who are highly optimized and willing to co-GP with you.
Whoever it is, they're not a name in your deck. They're evidence. For every person on your team slide, fill in five things:
Person → Relevant Execution → Actual Role → Evidence → Reference.
If a line only says "20 years in hospitality," you have a claim, not evidence. And get permission before you present anyone as your partner.
Step 2: Secure an anchor investor.
An anchor investor is someone who has agreed to take a chance on you early.
In my experience they usually take around 10 to 20 percent of the total equity raise.
An anchor makes the rest of the raise easier. When another family office sees someone already in, it shows you have history.
One distinction: the anchor investor's money isn't your money. Your own capital is the next step.
Step 3: Put in your own money.
Plan to be invested at least 10 percent of the equity check yourself.
On a $50 million raise, that means at least $5 million of your own money in the deal.
It's a lot easier to earn a family office's attention when your money is in beside theirs.
Step 4: Start with warm introductions.
Open your LinkedIn. For each family office on your list, find out who you're connected to there, or whether you share a mutual connection, what LinkedIn calls a second degree connection.
Then reach out to the people who already know that family office. Ask what you can do to get in touch. Ask them to put in a good word. Suggest a time to meet.
The ask is an introduction, not a check. The relationship comes first.
Step 5: Give the relationship time.
This takes time. You're not going to get a check within 90 days.
Expect 6 months to a year, sometimes longer, to build a good relationship with a group that would seriously write you a large check.
Step 6: Offer a true co-GP partnership.
Give the family office a way to come in as a real partner: a co-GP partnership where they share in the fees and share in the management.
Let them truly feel like a real partner. That gives them the best exposure possible to how you work, and it shows both of you exactly how you want to work together in the future.
If the experience is a great one, they'll want to do it again, because they've already partnered with you before.
Step 7: Be ready for diligence before they ask, and stay extremely conservative.
Know your numbers. Be ready before they ask questions.
Keep your projections hyper conservative, so that when you try to break the model, the model still works.
Hypothetical example of an extremely conservative projection: say the market exit for a potential deal could be around a 5.5% capitalization rate. Add 0.5, or even a full percentage point, to your projected exit cap. We don't know what the lending environment or the economic environment will look like three to five years from now.
Back that up with a sensitivity analysis that lays out conservative and aggressive scenarios side by side, so they can see how the deal behaves, not just what you hope it does.
Another hypothetical example, and this is the standard to hold: on an industrial deal where the market exit cap is 8.5% and you're projecting 9.5%, push the model to a 10.5% or even 11.5% exit cap. Add painfully low occupancy. Try to break the model. If the numbers still work after all that, you're ready.
That's the real test: you're trying to break the model, and it still functions.
None of this guarantees a $50 million check. It means that when you finally sit across from a family office, you arrive with an operator, an anchor investor, your own money, a warm path in, realistic timing, a real seat at the table for them, and numbers that survive scrutiny.
I learned that my $2 million raise could be too small for one room.
The answer wasn't to make the number bigger.
It was to become the kind of sponsor that room would take seriously.