Video library, Centimillionaire Strategies on YouTube

How to Build Trust and Complete Deals With Family Offices

Summary

Richard C. Wilson hosts Sahil Nandwani of Calafia Group for a practical conversation about reaching family offices, earning trust and moving from an introductory meeting to a completed deal. Sahil describes the family office community as close-knit and says investors respond to opportunities that stand apart, along with people who communicate clearly and follow through. He explains why capital raisers need to prepare for questions from someone encountering a deal for the first time, listen carefully, and send measured follow-ups. The discussion covers when in-person meetings help build personal connections, why a reliable counterparty can matter as much as the deal, and how specialization can help a business stand out. Sahil also discusses tailored AI tools, personal authenticity, overlooked market needs and targeted nonprofit work. Founders raising capital, investors screening opportunities and family offices building relationships can use these lessons to make conversations more useful and keep promising discussions moving.

Key Moments

Family office relationships move forward when you communicate clearly, follow through and bring an opportunity that has a reason to exist. In this conversation, I sat down with Sahil Nandwani of Calafia Group to discuss how investors screen deals and how founders can build trust with people who have limited time and many requests. His comments are useful for capital raisers, family office professionals and investors seeking better conversations.

Prepare for the Investor's Questions

Sahil's advice is to see a deal from the point of view of a person encountering it for the first time. A founder can know the product, terms and market so well that important gaps become invisible. An investor may have no context and may need basic points explained before weighing the opportunity.

Before a meeting, walk through the presentation as if you have never seen it. Identify the assumptions, unfamiliar terms and details that require explanation. Consider what a skeptical but fair investor would ask about the business, counterparties, structure and next steps. This preparation can make a conversation more direct and help you respond without rushing.

That work should continue after the meeting. Listen to what the investor requests and answer those specific questions. Richard described a common pattern: someone spends time networking and presenting, then stops responding when a straightforward follow-up is requested. That gap can weaken confidence in the person raising capital, even when the opportunity itself is promising. Our guide to mistakes fund managers make when pitching family offices covers related communication habits.

Follow up With Judgment

Follow-up matters, but frequency and timing matter too. Sahil described repeated messages sent close together as irritating. A short, relevant note can keep a conversation moving. Give the other person room to respond, then follow up in a way that respects the timing and tone of the relationship.

Richard shared how call summaries and brief video recaps can help a contact pass the discussion to a business partner, spouse or colleague. The useful part is clarity: capture what was discussed, what the investor asked for and what happens next. Use the channel the other person is comfortable with, whether that is email, a call or a text.

Responsiveness is also a form of due diligence. Investors are watching how a founder handles questions and commitments before they decide whether to spend more time on the opportunity. A missed response may be accidental, but repeated lapses can make the working relationship look unreliable. Family offices evaluating managers can use the same discipline when assessing who communicates well under ordinary conditions. See our guide to how family offices conduct due diligence.

Evaluate the People and the Fit

When screening an opportunity, Sahil emphasized the importance of the counterparty. A compelling deal can still become difficult if the people involved are hard to rely on or lack the ability to execute. Trust, competence and a workable relationship belong in the early discussion, alongside the business case.

He also described the value of in-person meetings. Video calls make it easier to connect across distance, but spending time together in person can reveal more about personal fit and help build a relationship outside a formal pitch. Not every conversation needs an in-person meeting. For an important relationship, though, founders should recognize that chemistry and familiarity can affect whether people want to keep working together.

Family offices receive many proposals, so a founder needs to explain why this opportunity fits a particular investor. Sahil looks for something distinctive, such as a specific market position or a need that others have overlooked. Investors can make their screening more useful by asking whether the deal is suited to their interests and whether the people bringing it understand the work required. Our guide on what family offices look for in a deal offers a framework for that assessment.

Make Your Difference Clear

Sahil connected specialization with the growing use of AI. As more businesses adopt general tools, a company's ability to adapt tools to its own work may help it stand apart. The broader point is to develop expertise that is specific to your business and to explain how it serves customers or investors. Founders do not need to follow every technology trend, but they do need to understand where their work can be distinct.

Authenticity can help people form stronger connections. Sahil described how experiences outside the usual investor profile can give someone a memorable perspective. A founder should be able to explain what they know, what they care about and why they are the right person to pursue the opportunity. The same applies to philanthropy: his family focused on communities where they had personal ties and could understand local needs.

For family offices, founders and investors, the practical lesson is to make each interaction count. Prepare for the questions you may not expect, respond to what was actually requested, assess the people involved and communicate the specific reason an opportunity matters. That is how a first conversation can earn a second look.

Full Transcript

Machine captions from the video, lightly cleaned. Names and terms may be misspelled; the video is the authority.

Show the full transcript

0:02 and then we're going to do a little um fireside fireside chat. So, Squil is a um single family office professional of an international business. Um they also work with other families. So, um they've actually started as a SFO and kind of moved it to a multif family office structure. He's a managing partner of the Colafia Group uh based right here in in Los Angeles, Beverly Hills, and he's overseeing the strategy for the family office, helping build out uh divisions of it, sourcing transactions and deals for it. He's spoken on stage uh several times at our events, and I've seen him speak before. And the reason we wanted to have Sahilter here today is just give a perspective not from a capital raiser uh such as Brian who comes out of a billion dollar family office um but Sahil's perspective on vetting deals getting to know people building trust um and we thought that might add a different different perspective for the day. So let's welcome Sahil up to the stage. Um we'll pass this mic back and forth because uh we're just a one mic room here today this way but that'll work for the film. So assume people will hear you perfectly. Yeah. But what else do you have in your your bio before you start?

1:12 >> Um well I would also add that that I personally have have been around the block in in quite a number of different industries. Um I started out in my first year of college. I went and I got my real estate agents license and I was working with very quickly started working with overseas investors and also in in the time intervening between that and and now I've also you know run the political circuit as well done a lot of training for a lot of uh candidates as well as done a lot of field work you know phone banking door knocking the text messaging and in fact one of the one of one of the big things that resonated me with me with what you just said is is the fact that you know the text messages do actually get a lot more response or or the voicemails because yeah when looking at you know mass emailing phone banking texting it was a lot of campaigns still haven't gotten to the texting bit even though it's very it's been proven that you've got so much more response rate there but a lot of people just you know the the inertia there of of not wanting to jump into new and maybe untested technologies for them. It it holds a lot of people back.

2:25 >> Right. Right. Totally. Um quick here. So, uh related to that, one thing our team started doing is um when we do a call, it's recorded on Fireflies if we do it on Zoom and it shoots them an auto transcript of the call and action items summarized automatically. And then our team also records a Loom video loom m just a minute and a half video summarized in the call showing on the screen what they might purchase or move forward on. And then that way they can share that with their business partner or their spouse or their team and there's a nice minute and a half summary of the deal that that's super helpful and be texted to people as well. Um so as a single family office, how do you approach those who are also single family offices um and you know are are very busy powerful people who like have a lot on their agenda, a lot of things coming in. How do you how do you approach them personally?

3:14 Um, well, it's weird because the family office space is such an insular environment. You know, you you start, you're a business owner, you start making a bunch of money, you go in, you start, you hear about what a family office is. It seems rather opaque. Um, then you create it. You go to communities like this and you realize there's people everywhere that are looking to either work with you or pitch you something or whatever. And it and it just gets me back to, you know, what I was always taught growing up, which is that, you know, there's there's money around literally every single corner. You just need to know where to look. But because there's money around every single corner, you got to be very focused about it because you've only got two hands with which to grab it. Um, so looking for those specific, you know, relationships or opportunities that are particularly unique that are, you know, this is not just a deal that, you know, there are 40 other, you know, real estate properties here, but only I can buy this one in this location and make it this kind of center for, you know, the community around it. you know, I can build something that and the money is just kind of secondary. That's the kind of people that I look for and and those

4:33 are the those are the people that that really end up connecting with smaller family offices like mine. Uh got to agree. Um in terms of uh something that we haven't talked about today, what would be the most powerful piece of capital raising advice that you could share with people here in the room? And it could be something that you see people messing up at our events all the time or just something that you found works really well. Um I people don't anticipate enough. People play a lot of halfcourt tennis. They think okay well you know what this is what I'm seeing about the deal. Um these are the things that I think people are going to be particularly concerned about. These are the questions that I'm going to prepare to answer. Um, and that's exactly the opposite way that you should be going about it because at the end of the day, you're not the one receiving the information and having to come up with the questions to then ask you. You've got to think about it from the perspective of somebody who has never heard of this before because you may have a fantastic deal with a fantastic structure. Maybe it's a little bit complex, but you know, if if this guy who hasn't even, you know, you know, even thought of this idea in his head, he's going to have a lot of questions that you're not going to anticipate

5:51 because you've glossed over them in your head. It's like read it's like reading um something that's printed in front of you in your head versus reading it out loud. you'll notice a lot more things that are hidden kind of between the lines because you're just scanning over, >> right? Um, what percentage of people that you meet in Family Office Club or elsewhere and you find initially relatively interesting and then either they do not listen to what you've asked them, they do not answer the questions you asked them or they just kind of fail to get back to you or they're just so slow to get back to you kind of write them off because like they're bad at listening or bad at followup. But what percentage of those do you think it is? >> Well, I don't want to indict myself cuz I'm pretty bad at followup, too. Um, but I would say most people um I would say at least at least 50 to 60% of people on the low end, you know, don't take that extra step because, you know, as as you mentioned, you know, you get 120 emails a day. How many second emails do you get to the people that you reply to?

6:57 probably half of the people that you applied to. >> Right. Right. Yeah. For sure. I've I've seen cases where speaking to somebody in our investor club and they need the capital. They for sure do need it and then Sil asks for something and then we just don't hear back and it's like they spend all the time to join family office club, all the time to come to the event, all the time to have lunch with Sahil or pitch him on a call and then some pretty simple things are asked for and then they just don't prioritize. It's like and he's saying like 50% of the time or more the ball is just completely dropped when it comes time for followup listening and paying really careful attention to what what the investor says. Uh we have a question in the back. >> The other side of that is there a followup rate that you find annoying like is there a follow-up rate that you find annoying? >> What frequent season?

7:50 >> I mean that that that's such an artistic question. Um, but there definitely is followup that is very very annoying. Um, every day, you know, if you like at least, you know, but give it if you're going to text somebody and then they don't respond to you, maybe you can give them a little follow-up text, but, you know, you can wait two or three days. You don't have to res you have have to go for it. You know, like your My dad will actually do this constantly. He'll he'll send an email and then he'll copy the email and then send another email but schedule delivery for like a day later uh and then half a day later and just it's at at some point you just want to not do business with somebody no matter how you know you could be you could be Joe Williams but if you're if you're gonna piss me off you know >> right yeah totally yeah good point I had one person introduce me to a a shark on Shark Tank and it was very nice of him to do that. But um then he emailed me the next morning and I saw the email come in but I was traveling. Then he emailed again later in the afternoon asking if I got the email in the morning and then he texted me the next morning saying asking if I got the two emails the day before. And so like I know if I made any introduction for him now that

9:07 he's going to eat them alive and make me look bad because like if he thinks that's a normal follow-up like did you get my email an hour ago? It's like uh kind of no. I mean I'm busy right now right? Like so it's pretty normal um for like the more stuff you have going on in your lives, the more busy you are, right? Like weeks fly by sometimes. So um how much do you think it matters about meeting in person for you personally or for large family offices? At what point in the process should someone raising capital really press an inerson meeting and and how critical is that for you? >> Well, I mean for me personally, I mean I know you can't be everywhere at once. you know, Zoom meetings, telecommunications, it makes a huge difference in being able to being able to to connect with people and to get your point across. But I mean, nothing nothing beats the kind of in-person meeting because I think also, you know, back back to my time in politics, you know, half the time is kind of spent quote unquote screwing around. you're going to events, you're, you know, you're drinking with people, whatever. But at the end of the day, it's, you know, the people that you form the personal connection with outside of the work environment or outside of this, you know, particular these particular rules of engagement that you've jumped into. It's those connections that mean

10:26 way more than any of those Zoom meetings could. >> Got it. Great. Thank you. And as deals come in or you you get pitched different things, um you know, in your mind, what are the top two or three things you instantly look at just to like make your life more simple and eliminate things real quick? And then if it gets past that stage, um and you're actually like, I'm going to spend a little bit of time poking at this deal, what is that really upfront fast screening process to again knock out 90 95% of things that come to you? I mean, for me, I feel like 70 80% of the things that that I think of can kind of be knocked out by just um ensuring that the stability of the partner that you're working with or the counterparty that's bringing the deal to you. Because you can have the worst deal in the world, but if you have a good partner, you got a trustworthy partner, or you've got one that you know that really knows what they're doing, even if it goes sideways, you know that you're going to be taken care of. But if you've got a really really great deal and the person you're working with just you cannot rely on them, every single second of that is going to be hell for you.

11:38 >> It's great. Uh Larry Connor's a billionaire. He came on stage one of our events. You said every problem you have is probably a people problem and most of your opportunities are people opportunities, right? And so I think that's kind of connected to what what Zil was saying there. Uh what are a few of the best pitches you've ever gotten whether you've invested in them or not? Um what stands out about one of the two of the best pitches you've gotten in the last decade? Um well I'll think okay so the the company that um one of the companies that you brought to me actually Better Bath Better Body >> right >> um it they it had done an incredibly fantastic job of communicating at the outset its perfect positioning within the market. You know there's it's it's Epsom salt market bath salt products very very small in terms of manufacturing. there's only so many players and right now especially you know going into more politically turbulent times having an entirely coming at me upfront with the information that almost all of his inventory and raw materials were sourced inside the United States and would be even even the down products would be you

12:55 know immune from tariff shocks which I knew were coming was extremely appealing to Great. Thank you. Um, so what are one or two trends in the family office space that might be good for people to hear that that you see being a family office they might not be aware of? And what is a trend with AI and how that's impacting um, family office investing? >> I don't know what to think about AI anymore. Um, because you know I'm I'm using it every day, right? I just I started like five or six conversations while I was sitting in the back there on on various things. Um but it is kind of it is getting to the point where you know if everybody is kind of kind of like the delusion of a college degree once everybody is starting to use AI it's this same brain everybody's got this 100red IQ brain next to it. It just means that you know your specializations are even more valuable. So I look at for example your AI tools. There are very very few businesses that are even exploring with custom GPTs to that degree. And whether or not custom GPTs themselves as a tool are strategically the right move like it's it's clear that businesses will need to sort of

14:15 customize and specialize tools for their needs that will map onto their specific business. Um, and it's hard to imagine where most businesses are going to to find the capital and the skill and the talent to put all of that together if they're not doing these these kinds of experiments. >> Yeah. >> Yeah. Totally. Um, we went deep on AI because when COVID hit, I realized we had to go from 32 events that year down to zero inerson events. Uh, and for like eight or 10 days, I was like, "Oh, you know what? What are we going to do?" And then realized, well, everyone has to do that. You know, Caressa has to do that. at Tiger 21 YPO it's like all right everyone has to so I need to pivot and adapt and the faster and harder I pivoted then the better a company would be and so anytime there's change it's the agile and the adaptive that do better and thrive and I think that's why it's important to be in the right community and have the right mindset otherwise it'll sit in the corner and complain about reality and complain about gravity but um with AI we're just trying trying to adapt in real time if any of you have spent a lot of time adapting to AI you want to trade notes on it and like he was saying I think it's super important um and it's going to become more and more important. So happy to trade notes on that. Um so in terms of family office networking um first of all if anyone has a big network

15:31 of family offices in in Dallas um you know I think he is growing his network in Dallas here um this year. So if you could be helpful to him we always talk about adding value to people first. We just talked about listening. So we have an amazing network in Dallas and he could help with that. I'm sure they'd appreciate it. But how do you think about networking as a family office? cuz maybe there's something that you could share here that people in the room could listen listen to and take away from on how your mind works knowing what you know about you know what your neighbors how your all the wealthy friends operate and work and and where they spend time etc. >> Uh I guess it kind of goes back to sort of the more personal element of it. It's, you know, I mean, cuz it's kind of a given in this room that everybody's got money, right?

16:21 To a certain degree, yes or no. But, um, if everybody has got at least this interest or at least this whatever in common, I want to know all the things that differentiate you from everybody else in the room. you know what are like for example for me right there there are a lot of people who have come up to me in these kinds of events or you know we've spoken about relative like certain political projects that I've been involved in because most people don't have that exposure to you know that world or at least in the kind of way that I do um or you know for example Michael right you and you and your wife you two come from the world of Hollywood there are very very few people that that I meet in in rooms like this one that have really much exposure at all to the entertainment industry. It's ridiculously fascinating and and those are the kinds of things that you know really do end up creating the strongest connections.

17:21 >> Yeah. Interesting. Uh Naval is a centillionaire out of Silicon Valley. I think it's founder of Angelist a couple other big platforms. He said that your competitive edge and advantage is being the most authentic version of yourself as a founder because your quirks and unique strengths are going to attract people who identify or want to associate with that. And if you put on a front that's not authentic, you'll attract the wrong people and then something's going to feel off as they get to know you better. Um he's also the one that said the highest form of intelligence, the only real sign of the highest level of intelligence is getting what you want out of life, designing a life that is getting you the results you want. Um is there any mental models related to you know family offices um growing your wealth growing business that you want to share like a favorite quote or a way that you try to operate or something that you you've realized recently and you put on your one pager maybe that whether you read that one pager every day or not or something you're like wow I'm going to do more of that because I just see the family offices I look up to doing that a lot.

18:25 >> Uh I I can think of a few things but I'll I'll go with this. uh negligence is the mother of opportunity. You know there's it it like there yes this world is more crowded than ever but that also means because things are moving so fast so many other things get pushed to the wayside and there are opportunities uh for people to innovate. Um think about for example Breeze Airways. Breeze Airways has only existed for what five or 6 years. It's one of the best success stories in aviation. And what's their business model? What do they do? They are specifically targeting non-stop routes that the other carriers not just don't usually service, but often don't service at all. Things like Brownsville to um to Orlando or Tulsa to NYC. You know, those are roots that no one would even have thought of before that actually nobody else, some of them offers, but Breeze has been able to capitalize on that specifically because they saw that nobody else was.

19:30 >> Awesome. Thank you. Um, any last questions for Sahil before my last one? Yes, in the background. What about fundraising for nonprofits? What do you look for in that space? >> So, the question is about like fundraising for nonprofits. What do you look for in that space? >> Um, well, I mean, there's part of that comes to, you know, personal stories of of how well connected you are to because because one thing that I've always been and my family has always been extremely anxious about in the world of nonprofits has been, you know, administrative fees, right? There are plenty of organizations that just act like large corporate organizations and they take a whole bunch of money that's meant to be going to you know the people. Um so if for example you're looking at uh at more targeted efforts for example you know when we wanted to give back for example and improve you know water infrastructure my family we didn't just look at you know any place we specifically went to the place where my dad grew up in Balid in the Philippines and we started working with first his high school and his college but also So

20:49 the other schools, universities, government buildings around that area specifically to provide them with better water infrastructure. Um, and I don't think any other organization other than the one we're working with would have the credibility to properly pursue that effort because nobody else is as well connected to the local infrastructure as our as our family is. Mhm. >> Got it. Great. Thank you. Um when you were talking about um advice, the question before reminded me of a quote by Charles Munger. He says the the first rule in fishing is go where the fish are. And it's kind of like the unfair advantage slide we had out there. I wonder before we end here and go to lunch, which I think is ready in the the next room over in the little mini kitchen they have over there. Um and then we'll come back in 30 40 minutes after that. What is something that we have not said today? I haven't said in my slides. you haven't said yet in this interview, but would just blow people away with massive value on how to work with investors, how to grow their wealth, how to grow their balance sheet.

21:55 Maybe something you feel like we don't talk about enough here or that you want to you want to emphasize to to end the interview. Um, so it's not something that you've that no one has mentioned here. It's something that Brian kind of dove in on a little bit, which is the celebrity aspect of it. Not exactly celebrity, but you know, something that I've said for a very very long time, and it's a little odd because I wasn't even alive to see this dissolve. But the posts Soviet fever dream is over. You know, the the period of luck, the period where you could just put money into a property and make money, or you could just give money to a wealth manager, to Goldman, to to Morgan Stanley, whatever, that's over it. Everything needs to be actively managed. Everything needs to be properly curated because so much so many more people have money. You need to be able to differentiate yourself in that environment. Not just with your investments, with your business, but with your personality, with your impact, doing things like that more custom personalized route of non of philanthropy and nonprofits. Um, it's those kinds of organizations and operations and projects that have a personality with them that will survive

23:12 the next 10 years, >> right? Like um there's a presentation on stage about um I saw something about Mr. Beast earlier this week. You know, the Super Bowl gets 250 million viewers and Mr. Beast twice a month puts out a video that gets 250 million viewers per video. Uh that's pretty mind-blowing. And 48 hours ago, I don't even know the guy's name, but there was an individual, he's 25 years old, he was unemployed, started creating videos 5 years ago, and he just sold the rights to his face and likeness uh for $975 million. So they can create a digital twin and put out videos in all different languages and license that twin for Starbucks commercials in India if they want to, etc. And they expect to make $4 billion off that deal this year. And so it's connected to what Sahil is emphasizing um and connected to some of the some of the things we're talking about today. I think that um one last thing that I'd want to comment on Sahil and if you have a a comment on it that's great as well. It's just Howard Mark says that when things are not going well is when you get better deals done you know and like what you said things aren't just going to automatically go up and if something's really toxic you might get it for a really good price or maybe you just bought something that's really toxic toxic and it was your worst investment ever. But this is Howard Marks, a multi-billionaire founder of O

24:29 Tree Capital, saying that a lot of the best deals are found during the hardest times. And it's that when you want to take extra action and adjust even more quickly and adapt and be agile so that you thrive while others are sitting around trying to figure out which way is up. You're you're driving and force and appreciation. Uh any last comments on that before we let people finally break for lunch here? >> Uh no, I think we can let everybody go to lunch. >> Great. Okay. Well, let's give a big round of applause for being here. Thank you.