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Host
Most lenders grind. Chris Pirro. He grows greens, raises chickens, surfs at sunrise, and still funds billion dollar deals before most people even hit snooze. From modular builds to hotel portfolios, church loans, cannabis, classic cars. Chris built a boutique powerhouse on the deals nobody else wanted.
Chris Pirro
I don't want to make a fee off somebody just to kick their pain down the hall. I probably could have, but I like to sleep at night. Right.
Host
A dad first, A lender with integrity, A renegade broker rewriting what boutique lending really means. This isn't just about rates and points. It's about presence, passion, and doing business in a way you're proud to pass on. From street sweepers to sharks and Pismo, this is the Chris Pirro playbook. Welcome to Coffees.
Co-Host
Right on. Thanks. Thanks for coming down to SoCal here. Hopefully the drive was nice and you know, we can make the best of it. Now, Chris, I like to start the show off the way I start every single show, which is, Chris, what's your morning routine?
Chris Pirro
A morning routine that's actually on my list here to go over. I mean, I'm a routine guy, which we can get into that as well. I'm, you know, discipline is freedom, I always say. So I get up in the morning, do my big cup of cold lemon water, splash my face with cold water, just try to wake up first so I don't hit the computer, the phone, you know, everyone says no phone or computer for an hour or two. I don't go that hardcore. But I start with that, have my cup of tea in the morning. I do like to get up early. You probably see, I don't know if you got my monthly mailers. I do get up at 5am I try to get my two hours in so I can get my day set up, set up my team and that way I can make my kids breakfast and hang out with them before they go to school. So I get my cup of tea. I'm not a coffee guy. I just can't work on coffee, get too jittery. And then I sit down with my notepad, I write down my to do list. So whether it's three items, five items, 10 items, I try to go through what's most important I did to, to accomplish and then, yeah, kids, breakfast. Usually I'll be able to work out after that. I've already gotten at this point, I said about two hours in of work and then breakfast, did a workout or a surf or depends on how the tides are. And then, yeah, just hit it from there. So routine, routine Routine.
Co-Host
Love it, love it. How close are you to the water in Santa Cruz, right?
Chris Pirro
Well, I can see the ocean from my deck. About 0.8 miles. About 12 minute walk from my house.
Co-Host
Nice.
Chris Pirro
Yeah, walk with the surfboard, don't walk with the surfboard. You know, I'm a longboarder, so you guys can have your own opinions on that. I'm too old to be a, to be a short border at this time of my life. But yeah, I like to go down. I have a E bike or I got, you know, a van, we have a B class van that we took out during COVID with the family. So I can throw boards in there and go down and you know, in this industry, I just put in my calendar, like surf, like it's a meeting. And you know, big clients, like, oh, from 10 to 11, you know, you call it a board meeting, right? I have a board meeting.
Co-Host
I love that. Love that. You know, one thing I'm surprised at with Searchlight lending is you've really built your business on like the difficult products. Now, you know, what is it that makes you say yes to the, to the things that, like, nobody wants to say yes to? Like, nobody wants to work with SBA loans in the mortgage space. Nobody wants to do commercial. No one's wanting.
Chris Pirro
No one. Well, good. You send them all my way. And that's why, I mean, that's, I think, why we've built a niche. I think they're, and I don't want to say too much as a connotation that they're more difficult, the connotation that they're impossible or there's different lingo, but a rate's a rate, LTV is ltv. Collateral is collateral.
Guest
Right.
Chris Pirro
So as long as you know, you're, I would say as long as you know what more than the borrower, you're an expert. So I guess to answer your question, why we say yes to it, I started by saying yes. So back in, you know, I started in retail, did my whole shtick at the big banks, and then started my wholesale shop. And someone says, hey, any SBA loan, any construction loan, I don't know what the heck I was doing. And I said, great, I'll get back to you in 24 hours. Hit the Google, hit my network, called bankers and said, okay, I didn't Even know what 504 versus 7A was at that point. And I get back to the borrower and I'm learning as I'm going. And then you learn during the loan process, right? I mean, the Best way to learn is to do the process. And by just getting those loans in, you know, after two, three, four, five years now I'm the expert and we can go in more into like relationships and how I'm leveraging and monetizing that. But just by saying yes then we could go into life. It's all about saying yes in life.
Guest
Right.
Chris Pirro
You know, you become the expert through experience. And now that's kind of what we're known for.
Co-Host
Now. In our research that we were doing about you, I saw that, you know, you've done cannabis, you've done, you know, cannabis loans. Yeah, yeah, cannabis loans. Churches, even airplanes. And art like that is so outside the box art. How do you, how do you get financing on art? How do you get financing on.
Chris Pirro
Yeah, so the art actually doesn't have to be held. A lot of the times. These are high net worth individuals and they're non recourse loans just based on their balance sheet. So we're not attaching anything to them. We're saying this person's worth $500 million net worth. We're giving them 50 million bucks and you know, an auto collection. We're not taking the pink slips. We're actually just going off their wherewithal and their net worth. We're assuming they're going to keep their net worth. So, you know, if something does hit the fan, you know, they have other assets that they'll liquidate.
Co-Host
So you use art. You collateralize the art. You collateralize?
Chris Pirro
No, I mean we're not collateralizing. We're not putting it. We will insure it, but we're not like putting it into like my basement, you know, in a lockbox.
Guest
Right.
Chris Pirro
It's still where it is. The same with cars and you know, all that. I mean, the planes and stuff will have to have UCC filings, like business filings. But yeah, it's really going over the financial strength of, and net worth of that. Of that individual or entity.
Co-Host
Right on. So what's the most unconventional deal you think you've ever done?
Chris Pirro
I've done some funny ones. I mean I did a street sweeper. You know, I did SBA loan for street sweeper. We did a barge for the SF bay that like dredged the bar. The, the bay. I mean I've done 2000 acres in Florida for a pre entitled development deal. You know, I could probably throw off. I was working on a hotel in Mexico with like Kenny Chesney and the Cabo Wabo tequila guy. So I like to work on. There's out of the box stuff is kind of funny. I mean I did the power exchange in San Francisco. If you know what that is, you know, you probably look it up. So we had to do a walkthrough on that. Yeah, you can look that up. I don't need to say what that was, but it was, you know, involves a gentleman's club kind of theme. But I really like the, the putting deals together where it's syndication plus equity investors. They're not easy, but it's fun seeing a lot of dirt go vertical to permanent to sale or stabilization and working with these people. They are professionals. They're developers and builders. This isn't a fix and flip in and we do that, don't worry the one off fix and flips. But these are people building large construction projects. We've done stuff in the billions of dollars and piece it together.
Co-Host
Nice, nice. Now being in the business 23 years, you've seen some funky stuff. What deal do you think still haunts you?
Chris Pirro
I mean the deals that haunt me are always the ones where the borrower client either is just shopping you the whole time is wasting your time, right? And I just like, I prefer when people are upfront and honest. I try to be the same way. If, you know, if I'm talking to an attorney or a doctor, I'll say, yeah, I'm getting a second opinion. These people ring you through, put you through the ringer and then at the end of it they're like, oh, I'm going somewhere else. And then they disappear with no explanation that just shafts my hide. It just be upfront and honest. It's a small lending world. It's just, you know, I like to sleep at night. I like to have good ethics. Tell me you don't like how my face looks or the sound of my voice or my rate was terrible, whatever. Yeah, just don't disappear. I mean, just be professional. I mean we're professionals. We have families like to sleep at night. You know, we're all people. It's not like just because you're through the email or the phone, the that you're impermeable. You know, it's just, you know, be nice and. Yeah, it's a small world. A lot of times they come back.
Co-Host
Later, I'm like, don't work with them again. Yeah, yeah, yeah. I've had that happen quite a few times in my career as well. You know, you came from big banks, right? Now big banks teach you a certain way of doing business. You know, the retail banking model. Let's say, and I think big banks are even different than traditional IMBs. Now what did you have to unlearn to really lead Searchlight in the right way?
Chris Pirro
I mean a big reason I left was because I could not do the out of the box or the tertiary programs. I mean they have a smaller box. If you're dealing with the big banks, we all know who they are. They want this kind of program, this kind of product, this kind of borrower. They want deposits, they want banking relationships, they want credit card, they want, they make the money on relationships. So you know, I hate turning deals down. I like to do the tricky ones. And really what switched for me was saying I want to be able to do everything. I want to help this borrower out. And when I go to do talks at like affiliate shops, whether it's an exp or side office, I say the reason why I work with a broker, full service is, is if your buyer or seller, let's say they, they have a broker and they're working with and they say, okay, I'm going to go to B of A and get a business loan. Well, that B of A person probably has a mortgage person that probably knows a realtor. You might just lost your real estate relationship, right? You might lost your transaction. So when I go into these affiliate relationships with either other mortgage offices or with realtor offices, I say we can do everything under the sun. And that way when they come back, we track them in our CRM. It was a lead source. Two years later this borrower comes back or client and they say I want to sell my home. I say, oh this is from XYZ Realtor. So I'm relationship, relationship. Keep it in the family, keep it in the circle of trust. And I think that's really got us to where we are right now is just giving back, keeping people in the circle and relationship.
Co-Host
Now you'd like to offer, you know, your, your no doc loans, DSCR loans, stuff that like brokers, they don't like to touch. Right? What, what take on that kind of fire or. And what's your take on that kind of fire? And how do you protect yourself from these funky deals?
Chris Pirro
I mean I am, I do lose deals sometimes that there is a less ethical broker on the other side and I'm okay with it. If the person truly cannot afford their payment and, or they're getting funky on their income or they're, you know, it's. I'd say here's an attorney's phone number. Let's go sell your property here's a realtor's phone number, get a price. Like I don't want to make a fee off somebody just to kick their pain down the hall. Like I rather. And I have people come back to me, they're like, oh, I got to learn somewhere else. And I'm like, almost like, I'm sorry but you know, I probably could have. But I like to sleep at night. Right. I don't want to put people in a worse pain point. So I understand if there is a borrower that has bank statement income on a non QM loan and they really show income, but if they just can't qualify for the property or if they're behind on their current payments and I'm going to put them in a higher interest rate, how are they going to keep up for their payments just because I gave them six months of interest?
Guest
Right.
Chris Pirro
So I don't like to make things worse for people. You know, you try to stay ethical, it's easier. Maybe the people, they need that check to pay their Mercedes payment or their, their house payment that month and you know, you can't, you don't know what other people are going through. But I rather just you know, not, not make money on other people's backs and their equity.
Co-Host
Love it. Now what's the most unconventional deal that you've ever funded and what do you think it taught you?
Chris Pirro
Oh, might take me a second, come back around to that. But most of my stuff that comes my way because I did have the nine years in retail, I'm kind of known with my retail buddies at the big banks as the A la source guy or out of the box guys. So most of my stuff doesn't fit into that box. So maybe the permits aren't in place yet. I love doing construction. Right now we're doing manufactured modular home. We've done, I mean I really like doing business loans because you're helping a business expand. So we're doing some stuff right now in the fireburn areas right now, putting together investors, athletes, people that want to invest in the rebuild.
Co-Host
So you're doing business, true business loans, not dscr, like actual business business loans? Yes, not collateralized.
Chris Pirro
Well, these people are putting together a fund then they're going to try to buy the fire areas and rebuild. So they have, they do stick build off site. They're going to come in and build for cheaper than they can build on site and they're putting, together, they're putting together local people to help fund the redevelopment and the rebuild in the fireburn areas. So we're putting together $100 million plus fund to work on that right now. So if anyone's interested, we're still having people come in, but there's athletes, musicians and we're putting together local people so the insurance companies don't come in or the vultures come in and just snake these lots away from the community. So that's, I mean I'm working on some pretty decently sized big stuff. And it doesn't always go through, but it still teaches you stuff. It still builds your network. You're still talking to people with high net worth. So even if it doesn't come together or they go somewhere else and not always, especially on the bigger deals we know they kind of, you know, they don't always go through but you're still learning during the process and you're getting contacts and relationships. So I like piecing together big deals, whether it's bringing investors together, high net worth individuals, you know, builders, people that experience.
Co-Host
Now I mean it's crazy because we were talking earlier, you got 100 agents and half of your revenue comes from these non conventional deals. So you really have become this like niche lender, you know, Because I don't know anybody in the entire industry that makes half their money on these, on funky products where you just take basically the toughest deals and make a true like a high income off of it.
Chris Pirro
Yeah, I mean especially in this lower volume market. It's worked out really well. It's worked out well for our recruiting. It's a good value add. When I say you know everyone, I must say everyone's the same stuff. But there's so many wholesale lenders out there, so much technology out there, CRM, AI, we can throw that around. But when I say you can come over here and you do multifamily mixed users, commercial special, you know, assisted living, hospitality. So many times a loan officer comes over and says, I just lost a land deal, I didn't know where to take it, I just had a construction deal, you know, I could have made X amount of dollars. So especially this lower volume market, it's a good sales point and recruiting tool to bring over as agents. And it's kind of like a flywheel effect. The more we get, the more we're unknown. You know, I'm on, I'm on realtor lists and offices, the out of the box guy. And yes, we do the conventional stuff and most of our agents are 90% residential first. But that's the value add with myself and Searchlight is we can train them whether we take it over as a referral or we take it over, you know, and keep them on communication so they can learn or tell them, you know, summary needsless, what kind of applications? And that's kind of like I said again, the value add is that we have specialized in that and now we're known as that. And I think it's. People can keep thinking it's harder than a conventional loan, but le CD trid cool off with all the new regulations. I mean, residential loans aren't that easy either these days.
Co-Host
Yeah, that's true. Now I just, I'm curious, like, what's the biggest deal you've ever done in this unconventional space?
Chris Pirro
I mean, I have a term sheet right now and a $1.4 billion deal. It's a bunch of flagged hotels. Portfolio of 100 flagged hotels. So working on that right now. That's interesting because we are not actually. We'll see if that comes to fruition. Not every deal does.
Guest
Right.
Chris Pirro
But that's too big to even put on a balance sheet. So we're going to put that together in a bond and sell it right to New York. So yeah, a couple, you know, 3,000 unit roundup here and there.
Co-Host
You've done something like that. 3,000 units, yeah.
Chris Pirro
But our biggest funded loan is probably in the 200, 250 million range.
Co-Host
Wow. Yeah, yeah. You're talking truly unconventional stuff. But like do you still make two points on a $250 million deal?
Chris Pirro
I wish.
Co-Host
Or a $1.2 billion deal?
Chris Pirro
No, no, no. And I won't say exactly what we make, but usually at that point you're making an eighth a quarter because most of these people can get institutional money or they have relationships with high net worth borrowers. It's almost like being in the broker space. If they have 10 million bucks at JP Morgan or Merrill and they're an a paper borrower, they're going to get relationship discounts. We're probably not going to beat them on a super jumbo purchase loan. We can't win everything, right? So it's this kind of same thing with these high net worth individuals. A lot of times they're flying on private jets with these banks and maybe they have relationships with high up people. We're probably not going to win that. But it's still the tertiary products, the people that maybe use up the credit at the bank or maybe have a blemish in their history or maybe aren't cash flowing so it's a stabilize. So there is still a niche market for Broker services. And I always like to use this, I hate to say sales line because it sounds salesy but it's like using a contractor. You can get your own plumber, build a house, get a plumber, you can get a painter, you can get a tile person, right? Or you can go to a contractor, which is pretty much a broker and say okay, well this guy trusts this plumber, he trusts this painter. So we get the Home Depot discount. We know we're not dealing with the teller at the bank, we're dealing with the VP or president at the bank.
Guest
Right.
Chris Pirro
So we have different rules, different qualifications and we get preferred pricing, dual relationships. So yeah, maybe you're paying us a fee for our services, but we're shopping around to hundreds if not thousands of lenders which most consumers have time for and we're getting you the best deal and it more than makes up for the fee that we charge for our services.
Co-Host
A lot of people talk about solutions based lending, right? You actually live it. So what's your brutal rule for turning chaos into, into closings?
Chris Pirro
I mean I like to. One thing I teach my team is really managing expectations. So if the borrower wants to close a private money owner rock deal which is a trid loan in three days. Not going to happen. It's a trid loan, 12 days minimum.
Guest
Right.
Chris Pirro
With cool off periods like day one. I almost treat it like a relationship or a marriage. If we're going to walk down the aisle together, it's not going to be that easy.
Guest
Right.
Chris Pirro
I'm going to need additional documents. I may need additional documents later. Don't yell at me. I'm here to help you because a lot of times you get in a deal with somebody and you haven't laid the groundwork for what the next steps are and what's going to happen and yes, they may ask for additional xyz, the appraisal may come in low. So here's what's going to happen Mr. Mrs. Bar or Client. You know, I've been, I've done enough of these, thousands of these and then I, I get the buy in, right? If you really want to work together, I want to work with you to the end because I, if you're working with somebody else, tell me please, right? You know, if you're dating somebody else, tell me please. It's such a relationship and you want to get to the end with a bar to understand the process. Because if you say yeah, I'll close in 24 hours and the rate's 5%, you know, it's not. You don't have a pissed off borrower. Right. And it's bad for your reputation. Work gets out, especially in these smaller circles with high net worth individuals, builders, developers. So I'd rather break up day one or hour one than three weeks into the process and they don't like me anymore.
Co-Host
That's good strategy. It's a good strategy. A lot of people just kind of cling on and then just get burned. Now you let's dive into some of your initial passions. You know what's crazy? You're a chef at heart, broker by trade, Right. Now, how does being in the kitchen sharpen your edge in the boardroom?
Chris Pirro
I mean, I'll start off by being honest. I've rarely worked in a kitchen. I did open a restaurant as far as the passion side, on the business side of it, I guess to sell a story because all my chef friends, I don't want them yelling at me that I wasn't in a crowded kitchen as much as, you know, maybe my bio says here. But I did open a restaurant. It taught me a lot about delegation. It taught me a lot about people in different slices of society, you know, just about business ownership.
Guest
Right.
Chris Pirro
Because you know, or we know mortgage. We grew it and lived it 20 plus years. We can do mortgage while we sleep. It's almost like we're in the zone. We do mortgage.
Guest
Right.
Chris Pirro
But cooking for me is more of a passion. And I was going to go to culinary school in college. My parents thank you, put me through a nice uc. I ended up finishing college. I went back to culinary school to start after my four year degree. And then my buddy actually brought me to a job fair right in the mortgage boom, 2002 and a half and I was in a suit college degree and I got an offer from HSBC that was way more than I expected. And I said do I want to flip burgers and work nights and weekends and holidays and I kibosh the working in a kitchen idea and then the rest is history. I was platinum club at Wells, top 100 person. And I guess I was good at it. It paid the bills. It afforded me what I wanted to do in my life, travel and all those fun things. And then I did have the bug still in me, the passion. I opened a restaurant and I did make it through Covid. It was four years but it's definitely. The passion was gone and that's a long conversation but I got it out of my system and now I'd rather just cook for my friends and family and loved ones. Because that way I can pick what I want to cook. I can relax at home. I can see the end product and the happiness and the nutrition and all that. I mean, I cook six days a week probably. It's like I can work 12 hour days and the relaxing part of my day is just put on some music, you know, maybe have a glass of wine and just cooking what I want for my family and loved ones.
Co-Host
Nice thing to cook.
Chris Pirro
I mean, anything on the grill. A barbecue. I got three different grills and smokers. Family loves ribs. I just made chicken wings last night. They love teriqi chicken wings. We do sushi night. I get sashimi grade sushi and do it up. It's hard to get all. You can eat sushi when you go out. We eat a lot, so especially my kids get older. My kids eating like 40 bucks of salmon sashimi. So I'll do lots of sushi.
Guest
Yeah.
Chris Pirro
And then we have a big garden. Like gardening is kind of my Zen as well, because I can be on a conference call with a client, have a big. I mean, I have so much kale and lettuce and tomatoes coming on my ears. Come bring a bag by. It's a you pick garden. But yeah, the kids will eat like anything out of the garden they can get their hands on, so. But I like to see them, you know, healthy, nutritious.
Co-Host
That's awesome. So you're teaching them the garden?
Chris Pirro
Yeah.
Co-Host
Eat off your own land?
Chris Pirro
Yeah. I say go pick whatever you want. Whatever's in the garden, you go eat. It's good. It's like, it's like the blue ocean thing. Right? It's like community, keep moving and then like have your own food source. Right.
Co-Host
So how much of your own food do you eat besides the garden? Do you have like chickens? Do you have eggs?
Chris Pirro
We do have chickens. My wife's in charge of the chickens. So he's got 10. We had five or six. They had their, their run. They lost about three years while they're producing eggs. And we just got 10 more chickens this Easter, so. But that's my wife's department. So we share the.
Co-Host
Do you have a full farm?
Chris Pirro
No, I mean, we have some, some land. It's enough. I mean, I do have a ranch, which is a different story, but that's. Yeah, that's a longer story. But we have enough, you know, a three quarter acre. So we have enough to. Enough to feed our family of four. So usually I'm buying some, you know, meats and then having a big salad or kale. Or I did broccoli this year so I do all the greens and everything and then I'll add some protein on the side.
Co-Host
It's awesome. You don't get, you don't get that kind of land here in Orange County.
Chris Pirro
No, no, no.
Co-Host
I mean we tried chickens for a.
Chris Pirro
While but you need like a rooftop garden here to be perfect.
Co-Host
That's a big thing in New York, right?
Chris Pirro
Yeah, yeah.
Co-Host
Now Searchlight doesn't just like survive on each lending, it's like it's dominating in that space. Now what's right one regulation or policy or, or trend you're actively pushing right now?
Chris Pirro
Might have to think about that. I mean I'm not currently active. I was doing MBA and all these different events. I am networking groups like Bama and stuff like that. So I'm really into, I think talked about this before the cast here is I'm really into working with other broker owners, like minded people. I'm an open book. I like to talk about if my agents want to talk marketing I business planning, what books I'm reading, you know, et cetera. I'm an open book. Like I meet with other broker owners as almost advisors and I'm fine sharing information. What marketing is working, what marketing is not working. Here's my contract xyz. So I'm fine sharing that because I think especially in this broker world, anything helps. And to have a trusted community where people can, you know, have experiences whether good or bad, it helps you guide the company, you know, share business back and forth. If I, you know, I can't do this property or that property. So I really like building a strong network of other like minded broker owners and being able to share content and success and failures. I mean it's sometimes it's a lonely, you know, industry we're in. A lot of people behind phones or still working at home and to have a voice or like I always say my group Searchlight is a team or a family. You know, when somebody dies we know who they are, somebody's birthday, right? It's, it's not just you know, your NMLS MLO number. These are people with families. And you probably think the same thing sometimes you're like, wow, I have hundreds if not more people that rely on their whole, you know, livelihood on what I've built or what I support. And, and it's, you know, when I started this search like you know, 15 years ago, I was probably the second youngest one in the company. And sometimes I'm like, there's these people's livelihood they're putting the kids through college on the platform model. Lenders, marketing that I put together, you know, it's almost like sometimes it's exciting, sometimes it's daunting, right?
Co-Host
It is. That's right. You know, it's a lot of pressure.
Chris Pirro
Yeah.
Co-Host
Now a couple last questions. Now if you had to pitch Searchlights model in one sentence to a burnt out loan officer, what would you say would make them quit their job right now?
Chris Pirro
To keep it short, we have sources that will make you revenue for the loans you may be turning down right now.
Co-Host
Simple. Now a couple last questions. Now you've been fortunate enough to, you know, basically establish a pretty successful business on your own. You're obviously a grinder. And I asked this question to all my guests. It's how are you instilling that same grit, that same tenacity that you have in your children?
Chris Pirro
I prefer Hustler over Grinder, but maybe grinder has a worse term these days. I think the best way to is just by, you know, them seeing you work them seeing you up before they are and working them seeing you working out and, you know, working on your health, because health is wealth and without your health, you know, we don't have the energy to work.
Guest
Right.
Chris Pirro
So I think just by showing them, you know, what you're doing and showing them success, it's not. It's nice to get on vacations. I mean, I brought my family down here this week. I'm doing a, you know, meeting a bunch of people. I don't like leaving my family for more than one or two nights. I actually like my kids and wife. Of course, honey. So it's like, I think just by showing them, even bringing them here shows me that, you know, I can work and I have the life balance because we can all make more money, we could all work more, especially in this business. No one's telling you to stop. And just by saying, okay, well, I went surfing with my kids this morning, even though I was up at 5:45 on vacation, plugging in so I could be ready for meeting everyone today and, you know, just my general office work. So just show them by example, I think is the best way to do it. Whether I'm reading at night instead of watching tv, spending time with them, whether I'm doing little League or driving them to sports or playing. We would love board games and rummy and backgammon. Just bikes by, you know, living the right way that they see.
Co-Host
Love that. Now, what's a personal goal that you have for yourself? A family goal that you have for the family and a business goal that you have for search site personal goal.
Chris Pirro
Would probably be, you know, just keep the work life balance going. I think it's easy sometimes, especially in this, a little tougher market, lower volume market we're in to say I'm going to work more, but just having enough and being okay with having enough. Because most of us in this modern world we're in have more than enough and just being okay with that. I think over the last couple years I've stopped acquiring. I've done more divulging. You know, time's more important than material wealth and enjoying the things you already have. Whether it's the garden, whether it's time together at the simple things. It's, you know, just, just playing. I got a, I got like an adult Lego for me and my son. It's like a 2000 piece adult Lego pieces that are this big and so that Japanese wave and it turns into a frame that you put in the art wall. And it's like doing that has been so fun and relaxing. So it's really, I guess my personal goal would be being more present and just enjoying the things I already have and the things I've accomplished. Which sometimes when that carrot keeps moving, you know, we want to get bigger, we want to get more important. You're never going to get the carrot.
Guest
Right.
Chris Pirro
And you're just disappointed. And the next one was business or family.
Co-Host
You can go in any order.
Chris Pirro
I mean, family kind of just goes into personal. It's just time, right? You know, there's all these stats out there. You spend like 80, 90% of your time with your kids before they're like 12 or something if you count up all the time. So really just relationships, the family. I almost, I have like the dad fomo, right. I don't like to miss events and graduation, of course, but like sports and music and school this and that like I like to and which gives us, in our business, we have the flexibility being more or less self employed.
Guest
Right.
Chris Pirro
And that was one reason I left retail. Because when I was retail, I was single, younger, it was no big deal, hang out the office, you know, fun, whatever. But now I can cut out in the middle of the day if I need to see XYZ or if my kids are in junior guards in a competition, I want to go watch.
Guest
Right.
Chris Pirro
No one's telling me when to work. And yes, I have to pay for it later by working, but just really, I mean time with the family and yeah, it's been the best dad I can be.
Co-Host
Yeah, I mean, it's like these times are fleeting and I try to be there for every event myself. Even like now I'm like, not gonna be able to take them to jitsu at like 3 for a couple hours. I get dad FOMO too. I. I didn't look at it in that context, but it's so important to be at every single thing for me.
Chris Pirro
Yeah.
Co-Host
Last question. When you're in front. When you're in front of the pearly gates, what do you think God's gonna tell you?
Chris Pirro
Well, yeah, man, you finish strong here, don't you? I don't know. I think there's a couple things. You always think back of that saying you're never on your deathbed wishing you worked more, right. You want to look back and, you know, my uncle told me this thing. You never remember every dollar he made, but you remember every fish you caught. And me and my son love fishing. So it's like, I think to get philosophical, religious, whatever you want to call it, I think when you die, hopefully you die with your experiences and your memories. And the more you make, I mean, you're not gonna. You can't take stuff with you, right? You can be buried with it doesn't matter. But I think magically, to make it all seem like it has purpose and reason. You die with your experiences, your stories, your times, memories.
Guest
Right?
Chris Pirro
So, yeah, you're. Yeah, you're gonna die wishing you worked more, but, you know, but success is still there. And you need, you know, you can't pay your mortgage with love, right? It's like, you know, so there is. It all comes down to balance, you know? Balance, balance, balance. Hit that pendulum in the middle. When it comes down to it, right?
Co-Host
You know when you say you don't remember the money you made, but you remember every fish you caught, like, that hits hard for me personally because me and my kid, my boys, all, we love fishing.
Chris Pirro
Yeah.
Co-Host
We just caught a halibut like shark. And like my 5 year old just keeps talking about the shark he got. It's just amazing.
Chris Pirro
Yeah, he's in care if you got another 10 lo's recruited, right. He's not talking about that. Shark versus Life Ice. I actually caught a leopard shark and Pismo on Father's Day, so.
Co-Host
Yeah, yeah, we did too. We caught a leopard shark. Was it Father's Day? No, the night before Father's Day. Yeah, yeah, yeah.
Chris Pirro
So that was the same one, you know, it's our kindred shark.
Co-Host
Yeah. It's cool. He's like won't stop talking about that shark. I, I, I totally understand. I could care less about the money you make. It's like he'll always remember that first shark.
Chris Pirro
Yeah.
Co-Host
Yeah, that's cool. I, I really like that con. I really, that, that really hits me personally. Well, thanks so much. If people want to connect with you, how do they find you?
Chris Pirro
I mean, Our website is searchlightlending.com and email is always best. It's we can do Team Chris, because I do have a support staff team chris@searchlightlending.com and I think all my social media fun is on, you know, maybe some notes, LinkedIn, Facebook, Instagram, which my wife's getting me more into. But I'm catching up. But yeah, I mean, this email's fastest. If you have your loan request or someone that all out of the box stuff that you don't know where to place, or if you just want me to send our, our offerings or have a conversation or if you want, want to talk about smoking ribs or catching fish, you know, please reach out.
Co-Host
Cool. Thanks, Chris. I appreciate you coming down and it's been great chatting with you.
Chris Pirro
Thanks for having me. It's.
Guest
Sam.
Coffeez for Closers with Joe Shalaby: Episode Summary
Episode Title: The Guy Who Can Fund Anything: Chris Piro of Searchlight Lending
Release Date: July 11, 2025
Guest: Chris Piro, Founder of Searchlight Lending
In this compelling episode of Coffeez for Closers, host Joe Shalaby engages in an insightful conversation with Chris Piro, the visionary behind Searchlight Lending. Renowned for his ability to fund unconventional and challenging deals, Chris shares his journey, business philosophy, and the personal passions that fuel his success. This episode delves deep into the intricacies of boutique lending, ethical practices, and the delicate balance between professional ambition and personal fulfillment.
Chris begins by outlining his disciplined morning routine, emphasizing the importance of structure in achieving daily success.
Chris Piro (01:06): "I'm a routine guy... discipline is freedom. I get up at 5 am, have my cup of tea, write down my to-do list, make my kids breakfast, and then work out or surf depending on the tides."
Living close to the ocean in Santa Cruz, Chris incorporates activities like surfing and gardening into his daily life, which he describes as his "Zen."
Chris Piro (02:32): "I have a garden... gardening is kind of my Zen as well."
His commitment to a balanced lifestyle is evident through his hobbies, including cooking for his family and raising chickens, which contribute to his overall well-being and work-life harmony.
Chris Piro has carved a unique niche in the mortgage industry by funding deals that others shy away from. His company, Searchlight Lending, specializes in unconventional loans, ranging from modular builds and hotel portfolios to cannabis ventures and classic car financing.
Chris Piro (03:05): "We fund the deals nobody else wants. From church loans to cannabis, we're the go-to for the unconventional."
By saying "yes" to these challenging loans, Chris and his team have become experts in handling complex financial products, transforming what many see as impossible into successful ventures.
Chris Piro (04:46): "You become the expert through experience. And now that's kind of what we're known for."
A cornerstone of Chris’s business philosophy is ethical lending. He prioritizes the well-being of his clients over mere profit, ensuring that he does not exacerbate their financial burdens.
Chris Piro (00:24): "I don't want to make a fee off somebody just to kick their pain down the hall. I probably could have, but I like to sleep at night. Right."
When dealing with non-traditional loans like DSCR or no-doc loans, Chris maintains strict ethical standards, often guiding clients towards solutions that prevent further financial distress.
Chris Piro (11:08): "I don't want to make a fee off somebody just to kick their pain down the hall... I like to sleep at night. Right. I don't want to put people in a worse pain point."
This approach not only builds trust but also fosters long-term relationships with clients who value integrity over quick gains.
Chris has a knack for securing financing for highly unconventional assets such as art, airplanes, and even entire hotel portfolios. His flexibility and innovative strategies enable him to tailor financial solutions that meet the unique needs of diverse clients.
Chris Piro (05:12): "For art, we're giving them 50 million bucks based on their net worth, not attaching anything to the art itself."
One of his most ambitious projects includes a $1.4 billion deal involving a portfolio of 100 flagged hotels, showcasing his ability to manage and fund large-scale, unconventional investments.
Chris Piro (16:40): "I have a term sheet right now for a $1.4 billion deal... a portfolio of 100 flagged hotels."
Chris emphasizes the importance of relationships and networking in the lending industry. By collaborating with other brokers, realtors, and high-net-worth individuals, he ensures a steady stream of business opportunities and referrals.
Chris Piro (09:16): "It's all about relationships. Keep it in the family, keep it in the circle of trust."
His open-book approach with fellow broker owners, sharing strategies and successes, fosters a supportive community that benefits everyone involved.
Despite his demanding career, Chris places immense value on family and personal well-being. He strives to maintain a healthy work-life balance, ensuring he remains present for his children and personal interests.
Chris Piro (28:48): "I prefer Hustler over Grinder... showing them by example is the best way to instill grit and tenacity."
Chris’s dedication to family is reflected in his flexible work arrangements, allowing him to attend his children’s events and engage in family activities without compromising his professional responsibilities.
Cooking serves as a therapeutic outlet for Chris, allowing him to unwind and connect with his loved ones. His passion for culinary arts teaches him valuable lessons in delegation and creativity, which translate into his business endeavors.
Chris Piro (21:26): "Cooking for me is more of a passion... I can relax at home and cook for my family and loved ones."
Additionally, his love for gardening provides him with a sense of peace and accomplishment, further enhancing his ability to manage stress and maintain focus in his professional life.
Looking ahead, Chris aims to continue fostering work-life balance while expanding Searchlight Lending’s reach in the unconventional lending market. His personal goal is to remain present and enjoy the fruits of his labor, valuing time over material wealth.
Chris Piro (30:32): "My personal goal would be being more present and just enjoying the things I already have and the things I've accomplished."
He also aspires to strengthen his network of like-minded broker owners, sharing knowledge and experiences to collectively elevate the industry.
In a poignant reflection, Chris underscores the importance of meaningful experiences over financial success, advocating for a balanced approach to life and business.
Chris Piro (33:12): "Success is still there, but you need... balance, balance, balance."
His philosophy resonates with listeners, emphasizing that true fulfillment comes from the relationships and memories we build rather than the wealth we accumulate.
On Ethical Lending:
"I don't want to make a fee off somebody just to kick their pain down the hall. I probably could have, but I like to sleep at night. Right." ([00:24])
On Building Expertise:
"You become the expert through experience. And now that's kind of what we're known for." ([04:46])
On Networking:
"It's all about relationships. Keep it in the family, keep it in the circle of trust." ([09:16])
On Work-Life Balance:
"My personal goal would be being more present and just enjoying the things I already have and the things I've accomplished." ([30:32])
On Life’s Priorities:
"Success is still there, but you need... balance, balance, balance." ([33:12])
For those interested in exploring unconventional lending solutions or connecting with Chris Piro, you can reach out via:
This episode of Coffeez for Closers offers a profound look into the mind of a lender who defies traditional norms, prioritizes ethics, and maintains a harmonious balance between professional endeavors and personal passions. Chris Piro’s journey is a testament to the power of integrity, innovation, and the enduring value of meaningful relationships.