Beyond the Case
A podcast where global leaders from the Harvard Business School Owner/President Management (OPM) community join in a personal capacity and share the real decisions, failures, and mental models behind building enduring companies.
This podcast is independent and not affiliated with Harvard Business School.
Beyond the Case
Personal Guarantees, Family Wealth, and Knowing When to Sell | Henry Maksoud Neto
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Henry Maksoud Neto took responsibility for his family’s Brazilian business facing roughly $250 million in debt, 600 employees, and a disputed succession. He shares the personal cost of trying to preserve a family enterprise, how emotional attachment can put family wealth at risk, and why succession cannot wait until the founder is gone.
Henry also recounts the OPM conversation with Professor Ananth Raman that helped him regain his resolve, explaining why the program’s greatest value was the wisdom and relationships it offered. Now based in Milan, he draws on that experience to advise owners through difficult transitions. His perspective is shaped by the realities of doing business in Brazil, where borrowing costs, bureaucracy, and legal uncertainty complicate decisions about when to fight, restructure, or sell.
Here are the Top 10 Takeaways from the conversation:
- Work with integrity and understand the problem more deeply than others expect.
- Plan succession while the founder can still guide it.
- Preserve the freedom to sell before circumstances force your decision.
- Avoid personal guarantees that put your family’s financial security at risk to sustain the business.
- Build your strategy around the economic and legal realities you face.
- Seek mentors who challenge you to act when you feel defeated.
- Invest in relationships that offer wisdom beyond technical knowledge.
- Turn hard-earned experience into guidance that helps others.
- Use technology to execute ideas grounded in your own judgment.
- Prepare for uncertainty without living every feared outcome in advance.
Books:
Hey, welcome everyone to another episode of Beyond the Case. This podcast invites global leaders from Howard Business School's OPM community, where they participate in a personal capacity and share the real decisions, life principles, and mental models which go behind building enduring companies. Today's guest is Henry Maksooth. He was part of OPM 51, which he completed between 2016 and 18. Henry, it's a pleasure to have you on the show.
SPEAKER_01I've been a pleasure for me for you to have invited me. Thank you very much.
SPEAKER_00Yeah. Yeah. Henry, could you introduce yourself, talk to us about your background and what you do?
SPEAKER_01I'm in my family established, my grandfather established a family business here in Brazil on the 50s. It was an engineering project company that did a lot of work in South America, China, and in uh Portugal and Nigeria as well. Projects of airports, dams, roads, buildings, hospitals, project. It made the project and implementations of the projects during the 50s, 60s, 70s, 80s, and 90s. Also, my grandfather at the time for expand our group, he made some verticals like hotels, farms, software companies, publishing all here in Brazil. On the 90s, the government uh swift here in Brazil and it was hard to maintain. We had 10,000 employees, and the economy was not like this. So we made a big divestment and closing of unities that were not profitable and remained with the hotel business. This is on the 90s. My grandfather passed away in 2014, and I uh the company had 250 million in debt of this large conglomerate, and I divested all parts of this conglomerate and sold the assets, and now I don't have anymore the family business. So in 2022, after COVID, we entered in Chapter 11 here in Brazil because the remaining part of the business was the hotel, and it suffered a lot during COVID. And during Chapter 11, we we made a big negotiation with all creditors of this 250 million that was from this operation of this company since the beginning. These uh debts came along. And only in 2014, where when my grandfather passed away, we had clarity about the total situation of the group. So I did this all restructuring, and gratefully we we we could pay the majority of the creditors, we still have some tax debts that I'm reorganizing. After that, I I moved to Milano, and because Milano is very in central of Europe, so you are close to Asia and close to America, and I started advisory for myself with all the knowledge that I uh I gained through these years to help owners family business during transitions. So I help during negotiations, succession, divestment, legal bottles, and all kind of all kinds of things. So that's a little bit of my quick history.
SPEAKER_00Thank you. That's very, very detailed, Henry, and it gives us a good insight into your journey. You spoke about being in the hotel business as well, as a family business at some point, and then you know the debt going quite high. Do you think somewhere newer forms of business models like we've seen, you know, Airbnb, etc., were a form of competition that your business felt was uh taking market share away from you?
SPEAKER_01Yes, of course. Uh Airbnb took a lot of market share. I think that Airbnb should change its strategy to enhance technology. Like, why didn't they build a lock that is universal that a person puts in their house? And with that with the code, one-time code, they when they buy an apartment in an Airbnb, they can use this lock. I think on these things, I think they should remodel their business.
SPEAKER_00When you were growing up, are there any conversations that you remember with your grandfather or your father around business that uh have since since stayed with you? Of course.
SPEAKER_01I was raised by my grandfather when when I was six years old. My grandfather, my parents got divorced, so I went to live with my grandfather and grandmother. So I passed all my life with him. That's why I succeeded him in the business, and because I worked with him all the time. Work hard with integrity, with honesty, work hard, work more than others, learn more than others, be ahead of everything. So I think this is the main thing that I learn and I use nowadays. I try to be in things that I'm doing, like when I'm advisoring a group, a family business. I try to learn more of the problem than the owner knows he has.
SPEAKER_00And what are some of the challenges that you see some of your clients face today when it comes to managing the businesses that you might be advising them on? Uh succession.
SPEAKER_01Majority of the groups in the world, they don't have a succession plan. This is incredible how it is. Dysfunctionality in families and when they need to make divestment, especially here in Brazil, in Italy, you have lots of bureaucracy to cross uh to make this divestment. So these transitions I call all this uh work transition. So succession is a transition, divestment is a transition, is a transition, business model transformation is a transition. I think it's it's this are the challenging things.
SPEAKER_00And do you think what is the right time in your opinion to have the conversation around succession? As soon as possible.
SPEAKER_01The success uh successful uh families that I I'm a great advocate of the the owner who tests their wealth during his life. And for instance, there's some families here in Brazil that did that. They're more successful families because they do during life. It's like, what's the best day to plant a tree? It's it was yesterday, the next best day is today. So I need I think that owners and parts of the family needs to talk about succession as soon as possible.
SPEAKER_00You are also quite uh active on LinkedIn, sharing your thoughts on a number of different points. And uh you've spoken at some point about uh you know recalling an OPM professor's warning around personal guarantees, which which almost everyone in the room must have signed, you know, in in an OPM class. So could you how do you think about the boundary between commitment to your business and responsibility to your family? And why have you spoken against personal guarantees?
SPEAKER_01We owners of family business get in love so much with uh our our businesses. Was talking to uh uh a friend uh in on this weekend. He he all his uh wish was to sell his company. And I was talking to him this weekend and said, No, I'm opening restaurants and so long. I said, Cristiano, you you got in love again with the business, no? He said yes, I did are meant to be sold. And when you get trapped, the economy is cyclical. And one time you don't have any more assets to so you you start to give your family assets to your your personal assets to to get uh finance or cash flow or something. It's difficult. It's better to sell the company. I saw uh this happen to my family. We don't have 5% of the wealth that we had 20 years ago because of that, because let's say sell that house, our house, to pay that debt starts to to go. And giving personal guarantee is a mistake, totally a mistake, on my point of view, of course. I'm humble to say perhaps there's somebody that uh has uh better knowledge on this, but I think it's a mistake.
SPEAKER_00But then but then there's this other side of the argument that hey, you have a family's name behind a business and you have to fight for it and do everything by it. And so, how do you talk to business owners who who come from that school of thought who say, you know, a certain brand name is what we have to protect, a certain family name is what we cannot tarnish?
SPEAKER_01As soon as I live in because I I I used to live part of the time in Brazil. That is uh, for instance, the interest uh the official interest rate here in Brazil is 15% right now. Companies are raising debt with 25, it's impossible to pay. There is nothing in the world that gives a margin of 30% that can pay a debt like that. It's going to destroy, you're going to lose the company. So I have a friend of my grandfather that always told me when my grandfather passed away, my dear, when you have an idea, you have to make this idea grow. When this idea is big, sell this idea because someone will try to steal your company from you. It's tough. It's different from country to country, of course. In US, you have less of this, let's say, this struggle of you have more competitive interest rate, you have less inflation, you have less bureaucracy, you have rule of law working properly. But in countries where anything can happen all the time, it's difficult. So you need to sell the business as soon as possible because sometimes things are going to get worse, and and I think it's in India is like that. I don't know if you can share your thoughts about uh India in this manner.
SPEAKER_00No, absolutely. I think having comfort with the legal system is very important, and you need to be able to rely on the legal system to feel that the fight is fair if things are not working out in your favor for the business. I think that's where the US and some of the more developed economies do such a good job of helping you separate the business from your personal liability, right? Uh and so if the business is not doing well, there are mechanisms available which you can notify the creditors of and then let that be a separate event from your personal life. I think in a lot of the developing economies, those regulations are still coming to play and they can continue to haunt you. Yes. Yes, yes, yes.
SPEAKER_01But uh it's because of this that we have a lot of opportunity to work on it. And I'm kind of specialized in these tough environments to help family business cross bridges in transitions, tough transitions.
SPEAKER_00And so your grandfather passed away in 2014, and 2016 is when you did your Unit 1 at OPM. Talk about what, you know, what inspired you to consider OPM.
SPEAKER_01Being very transparent with you, my grandfather passed away, the company was without liquidity. I had 600 employees to feed, and things were bad. I had uh my grandfather didn't make a proper succession, and there was a family dispute in the company, so I was so desperate that uh I saw I was looking for in Instagram, and I saw a friend of mine with uh a costume with the tie and with the paper saying Harvard Business School owners and businesses, owners and presidents management. I called him and said, What's that? He said, Oh, it's a program for owners and say, How can I apply? You you have to enter in the side of HBS, but they are going to ask for a person that uh you know that did this program. I said, I can I use you uh as a name? Yes, of course. So I applied at the same time, and I went there and seriously, it's I don't have it's tough to talk about OPM because it's the most important thing that I did for me in my life, besides, of course, my marriage, my two girls, and but this is uh it's amazing. It's amazing. It's not about the knowledge that you get from oh accountability, leadership, uh operations, sales, or negotiation. It's about the wisdom that you you get and the friends and then the friends that you make. I think it's okay. It's it's uh it's because of that that we're talking right now.
SPEAKER_00It's it's amazing. It's uh amazing. Are there any professors that left an impression on you from the OPM?
SPEAKER_01Anatan Anatan Haman. I don't know if you had classes. This guy for me he changed my life. I I went to do 101 with him, and I sent uh before because you have a 101, it's 20 minutes, perhaps 30 minutes. I sent him what I wanted to speak, and I arrived in his uh I knocked the door and said, Henry, one minute, three minutes, please come here. He said to me, Do you want me to cry for you? So beg your pardon, Professor, you know, because this is uh what you said, it's a sad story, but you look like you are finished, you're not going to fight. You're so I had had uh uh a person last unit that the guy was going to jail when he arrived to his country, and he was fighting. And what are you going to do? Then I I stayed with him one hour and a half, and this one hour and a half changed how I am right here.
SPEAKER_00I think his closing lecture has inspired and stayed with a lot of the folks from our unit as well. Yes. And I I heard that he's not teaching anymore. Yeah, I think we were fortunate. We might have been the last batch he interacted with. And yeah.
SPEAKER_01This guy is the person who he's an amazing person. He changed my life. Can't I can't tell how if possible, please send this video to him.
SPEAKER_00I will. If possible. Have you spoken since since that one-on-one you had with him? Have you been in touch with him? Shared, you know, any updates?
SPEAKER_01Yes, I I I I talked to him once and I I I I I think I talked to him twice, but I would love to reconnect with him, but sometimes I don't like to bother because they are very busy, you know. They they are uh sometimes I will write for him. But this guy, it's I want to write sometime uh uh article only about this conversation because it was poor wisdom.
SPEAKER_00The the writing skills that you have, is this something you've always had where you've you've gone deep into a subject or a topic and then expressed it, or has this been uh a recent development where you feel like you've understood enough about a particular topic that you have enough thoughts to centralize them?
SPEAKER_01No. I write, I don't know how to write, to be honest with you. I write uh very big thing, what I I need to write, what I want to write about what uh what is in my mind, and then I I use a lot of Claude to help me to write. All the content is mine, it's from my head, from my experience, from from my writing is execution. The strategy, it's what I want to write. The strategy, the execution, I I I use Claude to help.
SPEAKER_00If you could speak to a younger version of Henry today, having seen everything you've seen in life, what would you tell him?
SPEAKER_01I'm still a person that is very anxious, that tries to to strategize the future. Or if that happens, what I'm going to do, if not that I make diagram uh diagrams in my mind of a path, what is going to happen. I think it's sometimes useless to do too much thinking, too much. I will tell my you're be less worried because things will will give you an an example. I was during a dispute for one of our main assets. I fought with the person who bought our main asset in uh in a auction because of that. And I fought for 10 years with this guy that is a very, very, very rich Brazilian entrepreneur. Things went completely away what I was thinking as bad what bad was going to happen, but completely different in my favor. But I passed 10 years. Henry, do you like reading? A lot. I read uh seven books at the same time. Reading me one book, please. That has inspired you quite a bit. Meditation, Marcos Aurelius. This is this is uh the book. Everybody needs to read this book. It was written two thousand years ago, before Christianism, and uh it's pure wisdom.
SPEAKER_00Thank you, Andy. It was a very, very insightful conversation, I think. You were very, very forthcoming. So truly appreciate this, and I hope to meet you in person someday soon.
SPEAKER_01Thank you for inviting me. I very honor, very humbly honor. Thank you very much. Thank you, Andy. We are
