Funding the Unfundable: Jesse Holsapple on Hard Money, Bridge Loans, and Creative Lending Solutions

Steven Weinstock: 0:00 Hi everyone, and welcome back to the Wealth Clock with Steven Weinstock. I've been investing in real estate for over 20 years, starting with single family homes, scaling into multifamily properties, commercial assets, and eventually launching my own real estate investment fund. This podcast is brought to you by WE Capital and the Goethals Capital Fund, where we buy properties in cash. We lock in deep discounts, eliminate the mortgage risk in the first year, and we refinance later on in order to scale. But this show is not about me, it's about operators, the founders, and closers who are building real results in real time. Today's guest is Jesse Holsapple, the founder of Blue Mountain Capital, a national commercial mortgage brokerage specializing in private lending and hard money solutions. Jesse has built a reputation as the go-to resource for borrowers, brokers, and developers when traditional financing falls apart. From foreclosure bailouts to creative bridge loans, Jesse's team delivers the speed, certainty, and smart capital solutions across the country. Jesse, welcome to the show. Jesse Holsapple: 1:15 Thanks for having me. Steven Weinstock: 1:17 What is hard money? Let's just give a quick overview. Most of our audience probably knows, some people might think a couple of guys in trench coats show up to your door with a suitcase. Explain to me what hard money is. Jesse Holsapple: 1:32 Sure. In the old days, it used to be just a napkin deal, equity return. Maybe somebody could do the work, the other person could come in and write the check. Perfect teamwork. Nowadays that's a little bit more institutionalized. It's a little less strict than the bank, but people do still wanna know their money's going into a good deal. Asset based only still does exist in certain parts of the country as well, depending on your strategy with lower leverages. Steven Weinstock: 2:00 Walk us through your story. Where did your career start? Jesse Holsapple: 2:08 I was born and raised in Montana. Was in the banking industry, got into mortgages. A public company called Altisource was starting an origination arm for private debt. I applied to it. Up until that point, I thought that only private lending was somebody on HGTV that was writing a check and checking on their investment. Turns out there's an entire ecosystem around this and that really exploded from there for me. Steven Weinstock: 4:03 What kind of situations or deals typically come to you after the banks say no? Jesse Holsapple: 4:11 We look at A paper loan requests, the stuff institutional capital wants. That's really cookie cutter. We have competitive options for that. But I think where we've found a lot of traction was if somebody is in a position where they need to cross collateralize other properties to minimize out-of-pocket expenses, maybe somebody is in a foreclosure bailout but they're at a sub 50% loan to value. Strong operator, just unfortunate circumstances. We'll review it on our side before we entirely send it out to the market. Steven Weinstock: 4:55 And the riskier the deal, the interest rate or the fees go up? Jesse Holsapple: 5:01 Yeah. You will typically see a little bit higher on the points, a little bit higher on the rate for those risky deal types. You are asking a lender to essentially bail you out of a risky situation. Steven Weinstock: 10:04 So the broker is getting compensated for doing some of the legwork, finding this borrower, having the wherewithal to have a network of investors to bring it to, and they get compensated in the form of points and it's a line item on the closing? Jesse Holsapple: 10:25 Yep. Steven Weinstock: 10:26 Tell us about some of your worst deals in the last 24 months. Jesse Holsapple: 10:44 Most of our pipeline are hairy deals. We tend to like those because our need comes in a little bit higher. We're putting together an entire package with most, if not all, the documents that the underwriters will want to see. The worst experience was probably in the last couple of weeks. We had a closing fallout at the last minute. A totally separate lender was also working on a close at the exact same time on the exact same deal for a first lien position. I'm just thankful it didn't close. Apparently the borrower had been trying to close two first liens at the exact same time with two totally different lenders.