E332: Why Family Offices Must Go Risk-On or Go Broke

Summary

Podcast Summary: How I Invest with David Weisburd

Episode E332: Why Family Offices Must Go Risk-On or Go Broke
Release Date: March 24, 2026
Host: David Weisburd
Guest: Nate (Family office principal and founder of Barrel Ventures)

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Episode Overview

This episode dives into the evolution of family office investing, focusing on Nate’s journey from a century-old family food business to building a hands-on, alpha-generating investment strategy. The discussion covers costly early mistakes, insourcing vs. outsourcing, leveraging industry expertise, the misunderstood opportunity in food and beverage, venture capital vs. private equity, and passing down values to future generations. A consistent theme: For family offices, playing defense is not enough—"go risk-on or go broke."

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Key Discussion Points & Insights

Lessons from a Century in the Food Business

• Operational Brutality & Alignment:
  • The food industry is “operationally brutal” with thin margins and powerful retailers ([00:08]).
  • Lesson: Avoid misaligned incentives; long-term businesses are built on alignment, both in industry and in life.
  • Quote:
    • “Misaligned incentives are not the way to build enduring businesses in this industry or in life, for that matter.” (Nate, 00:20)

Evolution of the Family Office: From Outsourcing to Insourcing

• Costly Early Mistakes:

  • Outsourced everything at first; realized they paid fees for services they were as good at, if not better ([00:33]).
  • Transitioned to insourcing their core strengths, outsourcing the rest.
  • Quote:
    • “It makes no sense to pay fees on fees of things that we are as good, if not better at than people are going to be paying them to.” (Nate, 01:11)

• What They Insourced vs. Outsourced:

  • Insourced: Operating businesses in food and beverage (their “wheelhouse”).
  • Outsourced: Areas where they have less edge (e.g., public equities, tax loss harvesting).
  • "We sort of view ourselves as we're the buyer of choice for a lot of these businesses that we're looking at." (Nate, 01:58)

Building a Modern Family Office Portfolio

• Play to Strengths First, Defend with the Rest:
  • Elite family offices maximize their “alpha” where they have expertise, then hedge defensively against that exposure ([02:26]).
  • "Goal number one is don’t lose money. ...Our area of expertise... is food and beverage. Where we're going to take risk is in the area that we have the edge." (Nate, 03:01)

The Olipop Story & Barrel Ventures

• Seed Investment Process:

  • Early meeting with founders before first dollar in sales. Started with small checks, doubled and tripled down as conviction grew ([05:30]).
  • “The more you see team operate and grow a business, you get more comfortable with them and then we sort of double down and triple down…” (Nate, 05:53)
  • Result: Olipop became a multi-billion-dollar operation.

• Launching Barrel Ventures:

  • Spun out VC fund to focus deeper on food and beverage vertical; core value comes from operator expertise and network ([06:31]).
  • LPs in the fund are industry insiders—from ingredient companies to top farming families.

Leveraging LPs for Edge and Diligence

• LPs as Operating Partners & Advisors:

  • LPs help source, diligence, open customer channels, and mentor portfolio companies ([07:44]).
  • “These will be the first customers of our portfolio companies. These will be advisors to our portfolio companies. ...It's worked really substantially to the tunes of millions of dollars in sales, millions of dollars in ARR.” (Nate, 08:17)

• Top-of-the-Funnel Advantage:

  • Uses LP opinions in diligence before committing to investments. If LPs are excited, that signals strong customer interest ([08:56]).

Why Food is Underrated (Yet Rich in Opportunity)

• Key Points:

  • Ubiquity: The only industry humans interact with three times a day.
  • Antiques: Often “unsexy,” low margin, slow to change. But disruption is coming via tech, AI, and shifting preferences ([09:28]).
  • Fortunes to be made as new brands unseat incumbents (Olipop example, $2B+ exits with Poppy).
  • Quote:
    • "In a world where AI is going to eat and kill everything, I think [food] is the best place to be investing." (Nate, 09:37)

• Venture Returns in Food:

  • Multiple billion-dollar beverage exits. Smaller funding rounds mean capital efficiency and high multiple returns ([10:48]).
  • “Returns can be like the returns of a multi, multi billion dollar software or AI exit. But because they only raised one or two rounds of capital, a six or $700 million exit, which is a home run, can have the same sort of return profile.” (Nate, 11:18)

Pattern Recognition: Seeing Thousands of Deals

• Experience Matters:

  • Exposure to 1,000+ deals a year is essential for learning to spot founder traits and product-market fit ([15:38]).
  • “When you see a thousand, two thousand deals a year, you start to recognize who's full of shit, what are the traits that actually matter, who's going to really deliver and find product market fit.” (Nate, 15:44)

• Recognizing Product-Market Fit:

  • True signals: Customers “want it” and spread word virally ([16:42]).
  • Example: On a plane, a stranger tried their new product and immediately saw the benefit for his trucking company ([16:47-17:44]).

Founder Types: Functional Lunatics

• Defining Great Founders:
  • “There's a term I used earlier this year, functional lunatic. I want people who are functional lunatics, like people who are going to will this business to be successful.” (Nate, 18:05)
  • It’s not the absence of fear, it’s the compulsion to change the status quo ([19:04]).

The Generational Math of Family Offices: Go Risk-On or Fade Away

• Wealth Dissipation Over Time:
  • As families expand across generations, slices get smaller. Even 6–7% compounding isn’t enough with rising consumption ([19:41]).
  • "If you don't … transition from risk off to risk on, as the amount of people eating gets larger and the slices of the pie get smaller, you're not going to have any money left." (Nate, 20:49)
  • "It’s a math equation.” (Nate, 21:13)

Cultivating Values for the Next Generation

• Avoiding “Affluenza”:

  • Upbringing: “Money's not going to fuck us up. ...It’s as much a responsibility and a privilege as it is a good thing to have.” (Nate, 21:40)
  • Teaching: "Just because you can doesn't mean you should." (Nate, 22:16)
  • Giving back and involvement are important, but understanding the family story is the prerequisite ([23:01]).

• Passing on Values to Kids:

  • Even small acts (sharing birthday gifts, volunteering) add up over time ([23:36]).
  • “Those little lessons … subconsciously… they remember them.” (Nate, 24:06)

The Power of Networks and Giving

• Your Network is Your Superpower:

  • Initially resisted leveraging family connections, later realized that connecting people was his biggest strength ([24:39]).
  • “I'm one degree of separation and I just like connecting people generally even if there's no benefit for me. … Lean into that network and cultivate it.” (Nate, 25:09)

• On Giving:

  • “There’s two types of people in this world. There's givers and there are takers. Right. And I fully believe myself to be a giver.” (Nate, 26:12)
  • Importance of “double opt-in” on introductions to avoid burnout ([26:44]).

Final Message / Call to Action

• Look at Food
  • “As I said earlier, in a world that people are so afraid that AI is going to kill us all … what better industry to be invested in than something that literally can't be disrupted by AI?” (Nate, 27:34)

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Notable Quotes & Memorable Moments (with Timestamps)

• “Misaligned incentives are not the way to build enduring businesses in this industry or in life, for that matter.” – Nate ([00:20])
• “It makes no sense to pay fees on fees of things that we are as good, if not better at than people are going to be paying them to.” – Nate ([01:11])
• “We sort of view ourselves as we're the buyer of choice for a lot of these businesses that we're looking at.” – Nate ([01:58])
• "Goal number one is don’t lose money. ...Our area of expertise... is food and beverage. Where we're going to take risk is in the area that we have the edge." – Nate ([03:01])
• “The more you see team operate and grow a business, you get more comfortable with them and then we sort of double down and triple down…” – Nate ([05:53])
• “These will be the first customers of our portfolio companies. These will be advisors to our portfolio companies.” – Nate ([08:17])
• "In a world where AI is going to eat and kill everything, I think [food] is the best place to be investing." – Nate ([09:37])
• "I want people who are functional lunatics, like people who are going to will this business to be successful." – Nate ([18:05])
• "If you don't … transition from risk off to risk on, as the amount of people eating gets larger and the slices of the pie get smaller, you're not going to have any money left." – Nate ([20:49])
• “It’s a math equation.” – Nate ([21:13])
• "Just because you can doesn't mean you should." – Nate ([22:16])
• “Lean into that network and cultivate it because that is your superpower that most people don’t.” – Nate ([25:19])
• “There’s two types of people in this world. There's givers and there are takers.” – Nate ([26:12])

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Timestamps for Key Segments

• How Food Industry Background Shaped Investing Philosophy – [00:08]
• Family Office Mistakes & Evolution – [00:33] to [01:28]
• Insourcing/Outsourcing Strategy – [01:28] to [03:01]
• Portfolio Construction & Alpha/Beta Balancing – [02:26] to [03:36]
• The Olipop Investment Journey – [05:23] to [06:24]
• Launching Barrel Ventures – [06:24] to [07:33]
• LPs as Value-Adds and Diligence Partners – [07:33] to [09:17]
• Why Food is a Venture Capital Opportunity – [09:17] to [11:35]
• Pattern Recognition & Product-Market Fit – [15:32] to [17:57]
• Defining Great Founders – [18:05] to [19:24]
• The Generational Math of Family Offices – [19:24] to [21:13]
• Instilling Values and The Power of Giving – [21:21] to [24:29]
• Advice to Younger Self: Network as Superpower – [24:30] to [25:29]
• Philosophy on Networking and Giving – [26:12] to [27:14]
• Final Thoughts: Watch Food in the Age of AI – [27:34]

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Summary Takeaways

• Family offices must leverage their operational strengths and play offense in their area of expertise; generic portfolios cannot sustain wealth past several generations.
• The food and beverage industry, while long thought of as “boring,” is ripe for outsized venture returns due to shifts in tech, health trends, and consumer behavior.
• Pattern recognition, high-conviction founders (“functional lunatics”), and deep sector networks are the key differentiators for generating alpha.
• Philanthropy and value-based upbringing, not just wealth, are essential for long-term family office health.
• Networking and giving (with discernment) are powerful lifelong leverage points for investors and entrepreneurs.

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This episode is essential listening for anyone stewarding generational wealth, considering sector-focused investment, or building a hands-on, value-adding venture strategy in "unsexy" but enduring industries.

Transcript

[A]

Nate, so your family operated in the food business for nearly a century before starting a family office. What did that teach you about building an enduring franchise?

[B]

So this industry, more than others, is operationally brutal. There's thin margins in this industry, powerful retailers, working, capital pressure. And so it really instilled in me that misaligned incentives are not the way to build enduring businesses in this industry or in life, for that matter.

[A]

Last time we chatted, you said that your first 15 years of your family office were mired by many costly mistakes. Tell me about some of those mistakes.

[B]

Building success and wealth outside of the financial services. You are suddenly put into this position of, hey, you're no longer operating a business, now you're operating a family office, right? A financial industry. And so you need to learn expertise. And it's a drastically different operational world. And so we went from, you know, the first 15 years outsourcing everything and figuring out essentially what we didn't want to be to the past, you know, seven to 10 years saying, hey, here's what we're really good at and we're going to lean into our expertise and we can still outsource the things that aren't, you know, a core edge for us, a core competency. But it makes no sense to pay fees on fees of things that we are as good, if not better at than people are going to be paying them to.

[A]

So you started by outsourcing everything to large financial firms. You took a step back and you looked at what you're really good at, you insourced that and you outsourced everything else. What exactly did you insource and what did you outsource?

[B]

We said, we're never going to make alpha trading stocks, so we're going to use tax loss harvesting and sort of whole blue chips. But what we know how to do is operate businesses in our wheelhouse, which is the food and beverage world. And so we sort of said to ourselves, let's operate as a small middle market private equity firm, right? With the viewpoint of a family office that, hey, we don't need to flip these things in three to five years. We don't necessarily want to hold them forever, but we can have more flexibility and operate these from the perspective of, hey, we've been in these shoes before. We built businesses over decades and so we still invest in the typical family office things, real estate, private equity, stocks and bonds and things like that. But we, I'd say the past seven to 10 years have flipped to be a much more hands on operator perspective. And we sort of view ourselves as we're the buyer of choice for a lot of these businesses that we're looking at. You know, we have three platforms now and always looking at a fourth and looking to do add ons on those three platforms.

[A]

A lot of financial advisors will tell you to build this portfolio, this canonical portfolio of private equity, venture capital, private credit, real estate, etc. But the very elite family offices, the top 1%, they play to their strengths. They first start with where do they have alpha? For you guys it's food and beverage. For somebody else it might be biotech, for somebody else it might be venture. They absorb as much alpha as they can and then they have their the rest of their portfolio play defense on that food and beverage exposure. So maybe you're more hedged against food and beverage than a typical family office. Is that that how you went about it? And tell me about how you go about integrating your alpha with I guess the beta, the portfolio, for lack of

[B]

a better word, you know, as family office. We're not trying to create generational wealth. We've been really fortunate where that already happened. Right? Goal number one is don't lose money. That being said, we need to generate returns and build the assets. And so as you said, our area of expertise in food is food and beverage. On the operating side we've got these three platform businesses. And on the venture side, you know, the firm I run, the expertise is also in food and beverage. And so we say where we're going to take risk is in the area that we have the edge. Right, because it makes sense to lean into our expertise and we can get the highest returns in the area that we have the edge.

[C]

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[A]

so let's talk about your food and beverage investments. You were in the seed round for Olipop. Tell me about how that came about and how did you go about building your position?

[B]

I was an entrepreneur for a while and had a failed business and was sort of figuring out what I wanted to do next and was, you know, we had this good fortune of hey, we see a lot of deal flow just in this vertical because of my history and the family history and was introduced to the two founders eight years ago before they had done a dollar in sales, had one of them over for dinner and sort of viewed it as hey, this is going to be a portfolio approach. We're going to write a bunch of small checks into a bunch of early stage companies. In hindsight I wish I wouldn't have viewed it as a portfolio approach and you know, written every dollar. I had zero. Obviously you know we're very happy. But the first check was small. The more you see, the more you see team operate and grow a business, you get more comfortable with them and then we sort of double down and triple down and we've written a significant amount at this company and you know these guys have built an incredible business that's one of the fastest growing beverages of all time, exceeded everyone's wildest expectations to the nth degree. And you know it's a multi billion dollar operation at this point.

[A]

You decided to essentially spin out Barrel Ventures, which is a food and beverage VC from the family office. Tell me about that decision.

[B]

The first check we wrote was a Nollie Pop and it sort of spiraled from there. At its core, you know, I think as I've said I'm an operator and the family is operators. Right. And so we would invest in these companies and just because of our expertise and the network we have, we'd provide a ton of value. And so that spiraled from lollipop and was approached years later by some people who said, hey, you know, you built this track record. Would you ever consider raising a fund? And my first response was no. I think there are way too many people in venture with way too much money who don't necessarily know what they're doing and have drastically misaligned incentives. And I said, look, the only way I'd want to do this is if humbly, we could build a firm in a vertical where we could be better than anyone else, as that was the broader food world. And so I said, let's go see if we can raise a small fund in a vertical that we know better than most. And that was the broader food world. So pre farm to post fork and everything in between, all of our LPs, our families, corporate execs, kind of throughout this food and beverage world. And if you talk to every single one of our CEOs, they would say the value we add is more than anyone else on the cap table.

[A]

You do something that's quite unusual despite many GPS talk about it. You leverage your LPs almost better than anyone that I've talked to. Talk to me about how you leverage your LPs. How do they actually provide value in barrel ventures in your franchise?

[B]

We invest pre farm to post fork and everything in between. Likewise, our LPs are. We've got everyone from ingredients companies, packaging businesses, large 3 PLs, distribution businesses, brands. We've got one of the largest farming families in the country. And we talk to them and say, hey, what are some problems you're trying to solve within your industry or your business? Okay, let's have a thesis and let's go out and find something there. Or when we see interesting businesses, we look at them and say, hey, what do you think about company xyz? And then when we decide to invest in these companies, we sort of leverage our LPs as almost operating partners, right? And they're happy to do this because it is helping their business and helping their returns. These will be the first customers of our portfolio companies. These will be advisors to our portfolio companies. These will be mentors to our portfolio companies. And it's worked really substantially to the tunes of millions of dollars in sales, millions of dollars in ARR. I think one of our companies said, you're the only investor, and this is a company we've got a significant investment in. You're the only investor who's added more ARR than Metrex size and multiples of it, which makes me feel great.

[A]

Are you able to go top of the funnel and leverage your LPs for diligence and de risk before you even invest? Or is this just some value add?

[B]

After 100%, the first thing we're doing when we look at a company is let's look at our roster of LPs and who could benefit from this and what do they think of it, right? And if they like it, we're going to go talk to more and if they hate it, we're going to figure out why. And that doesn't necessarily mean we're going to invest or not invest, but we want their perspective because it's more valuable than, you know, their prospective customer.

[A]

Last time we chatted you said that food is a misunderstood industry and that there's much more opportunity than people realize. Why is food so underrated and what's the real opportunity?

[B]

It's the only industry in the world that every human being interacts with three times a day. In a world where AI is going to eat and kill everything, I think it's the best place to be investing. It's very antiquated, right? It is traditionally unsexy, right? Lower margin than SaaS, lower margin than software than AI. But there are interesting use cases where software and AI can affect these businesses to a massive amount. In a world of GLP1s and changing tastes and preferences and people caring more about their health on the brand side and the ingredient side, there are going to be fortunes made, right? Where you know, take you look at Olipop, right? Nobody thought that the world needed another soda. You know, they created this better for you soda category that is now a multi billion dollar a year category, right? Poppy was sold for $2 billion. You know, Lollipop will likely sell for more. And there's, you know, a dozen other competitors in the category. They're building substantial businesses. You look at something like Mac and cheese, right? Kraft had a monopoly. Then you got Goodalls and Bonza and all these other things and you know, they're taking significant share from Kraft. Consumer preferences change on irregular and there's going to be very, very significant businesses

[A]

built to play devil's advocate, isn't food more of a private equity play? You have low margins, you have very capital intensive. Why is it a space for venture?

[B]

That's a good question. If you look at beverage for example, over the past 15 years there have probably been 20 multiple billion dollar outcomes in beverage alone, right? These businesses, sometimes, a lot of times they can get to profitability earlier. Right. So simple mills sold for $800 million, but they only raised, I think, one round of capital, maybe two rounds of capital. Right. And so the returns can be like the returns of a multi, multi billion dollar software or AI exit. But because they only raised one or two rounds of capital, a six or $700 million exit, which is a home run, can have the same sort of return profile.

[A]

So another way, there's still room for these hundred x thousand x returns. There might be a smaller universe, but there's also a smaller amount of funds going after that universe.

[B]

Absolutely.

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[A]

Last time we chatted, you really stressed the importance of seeing a thousand deals before making a decision. Tell me about that.

[B]

This is a world of pattern recognition, right? And so when I first got into this industry, I was naive. And you know, you think everyone is the smartest person in the room and you think everyone is going to change the world when you See a thousand, two thousand deals a year. You start to recognize who's full of shit. What are the traits that actually matter, who's going to really deliver and find product market fit. And not to say that you're going to be right 100% of the time, but you start to recognize that there are certain characteristics of founders and certain traits and founders that you recognized with Olipop eight years ago that you now see in another portfolio company of ours nowadays eight years later. Right? And you recognize what are the early signs of product market fit, Right. What are the things that people are saying about a product that went vertical? And what do you recognize in a new product? You see what are the tech stack that these companies are using? Right? What are they, what are they solving problems for? How are they solving it? And what does product market fit look like?

[A]

What does product market fit look like at its very early stages? How do you know that company has product market fit?

[B]

I'll take another. One of our newest investments is a company called Ultra. It's a Zyn alternative nicotine free pouch company that is contains L theanine vitamins and nootropics to sort of give you that caffeine boost without the nicotine. This company in will likely do north of $75 million in their first full calendar year, which is absolutely insane. I was on a plane last week on the way home from Disney World, which I was exhausted and the guy next to me, I was next to two kids and the guy across the aisle from me put his in his mall and I had a full one of these in my bag. And I said, hey, try this. He said, what is it? And I explained it to him. So it's cool. I've been trying to get off this, right? And halfway through the flight he taps me on my shoulder and goes, you're now my wife's favorite person in the world. I just quit since I'm an ultra customer for life. Like that to me is product market fit. And then he emailed me after the flight and said, you know, he owned a trucking company and he said, how can I get this for every one of my drivers? They're all on zins all day long and all they talk about is how they want to, how they want to quit. You know, it's that natural flywheel of virality.

[A]

It's that difference between theoretically saying something's good and saying, I want it.

[B]

Yeah, now that I want it, I want to tell everyone I know about this.

[A]

You mentioned that you got a pattern recognition for Good founders versus great founders. What's that distinction between an A founder and a plus founder?

[B]

There was a term I used earlier this year, functional lunatic. I want people who are functional lunatics, like people who are going to will this business to be successful. It is their dream, it is their desire, it is their want. Like nothing is going to stop them from making whatever they're trying to build a home run. And, you know, if you talk to entrepreneurs, look throughout the world, like 99.9% of the world's most successful entrepreneurs are a little bit crazy, right? But at the same time, they're functional, right? And so, like, you need functional lunatics to build really big businesses.

[A]

They have a screw loose, but it doesn't keep them from burning down their company. They. They're able to function.

[B]

Yeah. I mean, to, to be an entrepreneur, you have to be a little bit crazy, right? You got to take crazy risks that the vast majority of people won't take.

[A]

Do you think for those entrepreneurs it's the absence of fear that most people have, or do you think it's really some pathological mental issue?

[B]

I don't think it's a mental issue, you know, because I've been an entrepreneur my whole life and I hope people would meet me and say I have mental issues. But it's also not without fear. I think it's a. It's this innate desire to change the status quo, right? To not accept what is out there and to say, there's got to be a better way.

[A]

Your family's almost a century into the food business, and the family wealth has now gone down several generations. You talk about family offices going from risk off to risk on which your family office is going through. Tell me about that transition. How does a family office transition from risk off to risk on?

[B]

It depends what generation you're in, right? There's the old adage of rags to riches to rags, right? And if you don't have unlimited money, money's not going to last forever. You know, as you get generation to generation to generation, if the average person has two and a half kids and our family's got many, many more, right? The. Well, G1 was two people, you know, by G4 can be 45, 50 people. And the slices of the pie get much smaller. And so to sustain a quote unquote, family office, you gotta increase the asset size, right? Especially as consumption rises and more and more people are becoming part of this. And so you need to figure out, what do we want to be? You got to think about this. In decades Right. Where do we want to be 10 years from now? Where do we want to be 20 years from now? We want to be doing the same thing. Do we want to split up? Right. By the time you get to G4, G5, you're talking about second and third cousins. Right? And maybe it doesn't make sense to have it all under one roof. Look, if you don't have unlimited money and you don't at some point from G1 to G5, transition from risk off to risk on, as the amount of people eating gets larger and the slices of the pie get smaller, you're not going to have any money left.

[A]

Family offices are default debt. If they continue to compound at 6, 7%, it's just going to be attrition. And by generation three or four, the wealth will evaporate.

[B]

I mean, the, you know, the, the story of rags to riches to rags, like, isn't a myth for a reason, right? It exists.

[A]

It's a math equation.

[B]

It's a math equation, right? And it's told generation to generation to generation. And I think it's a lot to do with values and how people are raised, but it's also a math equation.

[A]

I want to double click on that, actually. So you obviously come from a wealthy family, but you have that entrepreneurial drive. You have that entrepreneurial edge. So many billionaires and so many single family offices ask me, David, how do I make sure that my kids are not swallowed? It's like their number one fear. What did your parents do that instill that drive in you?

[B]

I remember, like, it was a very conscious and upfront thing of like, money's not going to fuck us up, right? Here's how we're going to act. And it's a as much a responsibility and a privilege as it is a good thing to have, if not more responsibility and privilege and to be philanthropic and to give back and to be respectful. And the, the lesson that I think about consciously and subconsciously every single day is just because you can doesn't mean

[A]

you should tell me about that.

[B]

You don't need to be loud, right? You don't need to spend everything you have. You don't need to. It's just a matter of how you sort of choose to live, right? Where there's a way, in my opinion and the way I was raised, there's like a respectful way to deal with success. And a lot of people agree with that and some people don't.

[A]

I had the former CEO of the Walton family, Steven Roach, and he talked about how giving in A family office is really critical because it provides a

[C]

purpose for the wealth and for the foundation.

[A]

Do you think that giving is a prerequisite for building this purpose and keeping younger generations from just spending all the money on frivolous things?

[B]

I wouldn't say prerequisite, but I think it's certainly very helpful. I think education is a prerequisite and figuring out, like, understanding the story, understanding the how, understanding the why, understanding the what. Right. If you don't understand where, where you came from and how things were built, then you just sort of assume like this is how it's been and this is how it's always going to be. Right. And you don't understand how hard it was to get to where you are then you don't. You sort of take everything for granted.

[A]

Nate, you have three kids. How are you raising them and what values are you instilling in them to continue family's legacy?

[B]

So I have a five year old, a four year old and a one and a half year old. My five year old in kindergarten. One and a half year old is not in school yet. Obviously my 4 year old's in preschool. It's something that we think about, right? And it's teaching them. You know, you get, you have a big birthday party and you get 25 birthday presents. Hey, you don't need all 25 of these things. Where do you want to give? Who do you want to give to? Right? It's volunteering. There's only so much you can do with kindergarteners and preschoolers, right? But those little lessons and the little things you teach them, one by one, they add up. And they, you know, subconsciously, when they're 7, 8, 9, 10, 11, they remember them. And it's these little lessons that they learned at an earlier stage that sort of helps them become really good kids as they get older.

[A]

There's nuance there because you want to wire their brain in a way where they're not being punished by having to give, but they're enjoying it. They kind of have this intrinsic motivation.

[B]

Exactly.

[A]

If you could go back to before you started your first company in the food business and before you started your venture fund. What is one piece of timeless advice you'd give a younger Nate?

[B]

You know, I was always someone growing up. I did really well in school. I did really well on tests, went to a great college. Coming out of college, I had no idea what I wanted to do. And if you asked me, like, hey, what are you good at? What are your skills? Like, I didn't have a Clue, right. Like I don't know, like what's my superpower? And I didn't know out of college I didn't want to use my network. Right. I wanted to sort of get something on my own, get a job on my own and not use the network that I had. It took me a little while to realize that my network is my superpower. Like if you talk to people who know me, spend time with me, like they say what's Nate really good at? Like I'm one degree of separation and I just like connecting people generally even if there's no benefit for me. I'm really fortunate that I did discover that you know, at an early enough age. But telling sort of the college Nate, like lean into that network and cultivate it because that is your superpower that most people don't.

[A]

Have you ever read the book? Never. You alone?

[B]

I think I have.

[A]

I'm preparing for my interview with Keith Farazi. It's one of the books that really influenced me 10, 15 years ago.

[B]

I need to read it again though.

[A]

In many ways we grew up on the opposite side of the tracks. I grew up in Section 8 housing as an immigrant. You grew up obviously in a privileged background. But one of the things that I learned early on is that the one thing that a low status person could do is actually connect two extremely high status people. That is the token that I used over and over to kind of build my network. And it, it's powerful and it's something that really compounds. As long as you have.

[C]

There's a lot of rules to it.

[A]

You have to make sure that's double opt in. You have to make sure that both parties are benefiting. It has to be something where you use the token. You get two tokens back versus use the token. Now it's gone.

[B]

And you've done an incredible job of that. This is an over generalization. But there's two types of people in this world. There's givers and their takers. Right. And I fully believe myself to be a giver. Right. Where I can't tell you how often that I connect people without any clear line of sight of how it's going to benefit me. But I believe that it's all circular and karma is going to come back to benefit me and it's worked out really well.

[A]

Have you fine tuned your system? A lot of givers burn out and feel taken advantage of. Is this a sixth sense you know when not to give and talk to me about that.

[B]

I don't have a system. I think it's like goes back to my superpower, this like innate ability and like photographic memory to remember where I met someone, how I met someone, what do they do, who are they connected to? I do think the double opt in is really, really important. Right. You know, I, I get in, there's someone I know that often makes connections and introductions with without getting a double opt in. And it really bugs me like because it's often to me and like it's something that it's a time killer and like a soul crusher. Especially from the other it doesn't benefit

[A]

anyone, including the person that they introduce,

[B]

especially from the other person's side because if it's hey, you should meet, you might be in like Nathan run. Nate runs a venture fund and so and so is running a business. If I'm not interested, it's just like why even send that email? It's better to stop it before it happens. Right? And so I think the double opt in is really, really important.

[A]

If you could ask for one thing from the community you're always giving, what would be one thing that you, Nate, could benefit from?

[B]

Our listeners pay attention to the food industry. As I said earlier, in a world that people are so afraid that AI is going to kill us all and in the world, what better industry to be invested in than something that literally can't be disrupted by AI? These are the most part they're physical products and AI will certainly help and make them more efficient parts of the industry. But you're not going to out AI food.

[A]

On that note, Nate, thanks so much for jumping on.

[B]

Thank you.

[C]

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