What are you waiting for before you finally take that first step?
On this episode of EPIC Begins With 1 Step Forward, Zander talks with New Zealand entrepreneur and property expert Hadley Nightingale about mistakes, uncertainty, analysis paralysis, and why waiting for the perfect moment can keep you stuck.
Hadley shares how an early real estate decision sent him on an unexpected journey from farming and working long hours in Australia to eventually building a successful property-buying company.
Together, Zander and Hadley explore why you don’t need every answer before moving forward, how experience changes the problems you’re capable of handling, and why consuming endless information means little without action.
They also dive into real estate investing, market cycles, finding the right mentors, and a simple truth: progress requires eventually stopping the research and taking the step.
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Stop Waiting For The Perfect Time—It’s Never Coming With Hadley Nightingale
I’ve got an international guest with me. Hadley Nightingale. Hadley, tell us who you are, what you do, and where you are.
Morning Zander. It’s bright and early here, down in New Zealand. Obviously, the great thing with being down here and you guys in the States is that bit of time. I’m based in New Zealand and own a company called New Zealand Property Buyers. I suppose in New Zealand, no one is the property guy. It didn’t always start out that way.
We’ve grown a company now from 0 to 13 people over the last 3 or 4 years, growing the business year on year from that. In the start, it obviously started out, made a fair few mistakes, learned the hard way, and had the struggle I think comes with, comes with going it alone without getting the proper help. From that, I suppose we started the business with the motivation of people not having to go through the struggle that we went through on the way up.
Look, mistakes are part of the journey. I always love to get a little backstory. Hadley, where did you start off your professional career, and how did you get into doing properties?
It started out farming. Coming up through school, there was always a thing that they were obviously going to become a police officer or a farmer. My mom really wanted me to be a police officer, and, being a rebellious teen at the time, I said, “I’m going to go farming instead.” I ended up going farming, and at that time I was like, “If I’m going to become a farmer, I need to buy some land.”
In about 2007, I went and bought some farmland and probably didn’t get the right advice around that. It’s been very similar to the previous downturn that we’ve had in real estate, where everyone’s like, “Not making any more land, prices are going through the roof.” It was just with the writing on the wall a second time around, except I got burnt the first time by getting sucked into it. I was on a bit of a mission to make sure that people didn’t do the same thing as I did the second time. Because of that, earning time, I think it was like $13 an hour with a $700,000 mortgage.
Escaping The Work Harder Trap
I had to go and find someone who was going to pay me $20 an hour, who was in Australia. I ended up flying over there, working in the cropping part of Western Australia, and then driving road trains and mining and all the things I could do because my philosophy became, “If I just work some more hours, if I push a little bit harder, then I can make some more money.” It turns out that you burn yourself up pretty quickly trying to run that path.
Absolutely. I was just going to quote Dr. Phil and go, “How did that work out for you? If I just work harder, if I only need four hours of sleep, I’ll make it.” We’ve all been there where if I just push harder, and that is not always, it’s like smarter, not harder. When I look back on my entrepreneurial journey and just, like, my whole career, I do so with a fair amount of gentleness because hindsight’s 20/20, and there are things that there’s no reason for us to have known at the time.
We look back and go, “Man, I should have known this.” I go back and go, “Why would I have known that? There’s no reason.” I have the experience now and go, “Boy, that was a mistake to buy that land at that price or whatever.” You had no prior experience. Why would you know any different?
No, I think exactly. It’s like lived experience, right? At the same time, think now with the internet. This was twenty years ago, when YouTube was not really a thing. Social media definitely was not there. People have a lot more options around learning stuff and finding people that they can, in terms of role models, coaches, and things like that.
Grinding more hours isn’t the cure for bad strategy. You’ll burn out long before hard work fixes broken systems.
We didn’t necessarily have more than a book or a CD at the time that was going to try to point you in the right direction. At the time, you do not know what you do not know. I do not think anyone ever sets out on a path to be like, “How can I royally stuff this up? What can I do this week to really get this wrong and really make a hash in my life and make things difficult for me?”
One thing that I talk about all the time and I see is paralysis. I need to have the answers to everything, and I cannot move forward until I have all of these things set up.
Overcoming Analysis Paralysis
It’s probably one of those things. Now, as I say, with the information, there’s so much that it does get paralyzed by analysis, and you cannot make a decision because there’s so much out there, and what do you do? One of the big things for myself, anyway, it’s just been like just trying to find one course or one person to listen to and go, “If this person’s successful, if I just follow one thing and do not try and dart and dive in the time that I have.”
Also, people are like, “I have to have everything set up before I launch.” It’s not to just go off without having thought about it, but all too often, people think about their epic journeys or starting a company or whatever. They never get anywhere because they’re waiting for everything to be perfect. The way I like to talk about it is, and I’ll just ask you this question, because I know you’re just beginning your day. Do you have all the answers to all the questions that you’re going to get today?
A hundred percent not. That’s part of the excitement.
Did that stop you from getting up?
No.
Whatever we’re doing, I do not have all the answers. I am going to fail at some things. I’m going to try some things, and they’re not going to work. It does not mean that I’ve failed. It just means, “That’s a way not to do it.” We could do all the research we want and still make a mistake. It’s just not our fault. Stuff changes. I used to work in the corporate world.
I worked in some startups, did all kinds of research when they offered me a job, such as the company Solid, how their funding, what their burn rate is, all of that. Get in, and still, due to no fault of my own, the economy changes, management makes bonehead decisions, and I’m out of a job. You, as a farmer, could do all the research about what crop to grow, I’m going to grow this crop, and I’m going to use this seed, and there could be things. It does not work. Your crop does not come in.
Why The Perfect Time Never Arrives
No, 100%. That’s life, right? Nothing’s guaranteed, and there’s always a surprise every day. You’re 100% right. If you sit there and you’re waiting for the perfect time, all you’re going to do is sit there and wait because the perfect time never comes. The thing, though, with experience is that the problems that you have, that I had eighteen months ago, that were big problems for me, today are not big problems because my experience has grown. I find that in eighteen months from now, the problems that I pull my hair out over today are going to be minor and insignificant things as your experience grows and you get better at what you do as well.
Now, I’ve got to say, I know very little about the New Zealand real estate market. I want to ask, how is the New Zealand real estate market? What have you learned? Even though we have a worldwide audience, there are some universal things about real estate that people might want to know.
A hundred percent. I do not think it matters where you are in the world. The philosophies and the principles remain the same wherever you are. Just the laws change slightly. It’s about figuring out how I can do things in my specific country or state rather than why I cannot do them. At the moment, for us, we had a huge ramp-up into 2020 and 2021. It’s very similar to 07 and 08 all over again. Now we peaked in 2021. In some markets, we’ve come back 25% to 30% off that peak.
The interesting part with it is that people we were talking to in 2020 were so bullish about the market and we’ve just got to get in, and if we do not get in now, I was sitting there thinking, “This is very similar to 12 or 13 years ago.” People tend to have short memories when it comes to markets rocketing. It also becomes a self-fulfilling prophecy at the same time, where they forget what happened back then, or it’s the first time they’re in a bull market.
The market takes off, they jump in, they get in at the top of the market, the market pulls back twenty percent, and they go, “This bloomin’ real estate thing does not work.” The market calls. They figure out what happened if they were only a little bit scared by it, and they get back in 2020. The market pulls back 25%. They told you it does not work. The thing with it is, when you’re in there speculating and when you’re in there for a short-term game, that’s going to happen.
Stop waiting for the perfect time to act. It’s never coming, but your experience grows once you start moving.
You buy at the wrong time. Yeah, it is what it is. You’ve just got to go in with buying things when things are in front of you, as opposed to going, “I’m just going to wait till the market crashes.” That was the other side of the argument. At that time, as well as I’m going to wait till the market comes back, I’m going to wait till the pullback. I’m going to go in and spend as much as I possibly can. The funny thing is, the markets come back 30%. People are sitting on their hands, going, “Property’s down. Why would I buy it now?” It’s down 30%. It’s the thing you were waiting for.
Good time to buy, in my opinion.
It’s the thing you were waiting for. Four years ago, it happened. It came true. Now the herd’s not buying real estate, so you should not do it either. As Warren Buffer keeps saying, “When everyone’s fearful, be greedy, and when everyone’s greedy, be fearful. Now for us is the prime time to buy. You’ve got to be contrarian to what the rest of the market’s doing.”
Look, I do not have extensive real estate investing. I do have a house. I’ve owned other houses and other properties. I guess the historian in me says, “Look, first of all, investment is a long-term, not a short-term deal. Historically speaking, real estate will appreciate. It will over time. You just have to try to be patient if you can.” When it pulled, like anything, stock markets, real estate markets, anything where there is a commodity. Commodities go up and down. Again, none of us can predict exactly. “It was great. We got it right at the bottom of the market. Now I’m riding it up.”
The Danger Of Market Speculation
People who play the bottom-of-the-market game generally tend to miss it. Generally, because they listened to the media and go, “The media has now said that house prices are moving. Therefore, I need to jump in now.” The issue is that I was talking to a journalist about this the other day, and her take on it is that we just follow what the data says. The data is 3 to 6 months behind what’s actually happening in the market. By the time they’re reporting that house prices are starting to move, house prices have already moved 2%, 3%, 4% by the time that the media is telling you that we’ve had a positive 0.1 or a positive 0.2.
Every year, I know this. I live in the San Francisco Bay Area, where real estate is, depending on where you are, literally ridiculous, like the prices. There are buying seasons. There are times when, if you’re thinking of selling your house, put it up for us. It would be put up in March and April because people who want to buy a house but they want to make the move over the summer so their kids can be in the school district, that’s when they’re looking. Do not put your house up in July. Again, there is no rhyme or reason. There are people who put up their houses whenever. They sell, and other people have beautiful houses, and they do not sell.
It’s one of those things. As for us, we’re obviously the opposite of you guys in terms of time of year.
It’s because you guys are in the Southern Hemisphere. I’m sure you guys have the same kind of, here is the time that you put up your house because people looking to buy a house want to do it at whatever.
Spring for us is the time that most people try to put their houses on the market because it’s coming into summer. December is one of the best times of the year for us, which is Christmas time, to go and do that because everyone’s more worried about having beers and having barbecues and doing their Christmas functions. Obviously, when it comes into autumn and then back into winter, the market slows down. It also runs with the seasons as well.
You just have your times where buying opportunities are great, and then you have your slower months where the market decides, or more people decide they’re going to jump into the market. Things for us can be a bit quieter. An opportunity becomes a little bit less. It’s about being aware of that and not getting carried away with the market at the same time.
It’s also understanding. Education is powerful. You’re right. There is so much information that you can get overloaded. I totally agree with listening to one or two people, right? If you’re going on YouTube and trying to learn about real estate investment, find someone who you think appeals to you. Again, different people are going to have different approaches to it. Find the one that resonates with you. Frankly, if the big voice out there is that person is not someone that you like a lot, do not listen. You do not have to just because someone’s the number one real estate person.
Maybe the way that they’re presenting stuff just does not appeal to you. It’s like with teachers in school. We all have those one or two teachers that are, “I really like Mr. Nightingale or whatever. He really explained it.” I didn’t like Mr. Sprague because he’s like, “What do you mean you do not get it? I just explained it to you.” Other people are like, “I want to be yelled at,” and you may be like, “No, I want more, like, understanding. Let me work with your approach.” The same is true. Look, if you have a real estate agent, find the one who works for you.
Filtering The Noise To One Voice
Yeah, 100%. That’s life. It’s finding your people, and not everyone’s going to like you, and you’re not going to like everyone. That’s just how life is. It’s really the thing to just find one path, find one person. If you’ve done a bit of research on them and, as you say, you think the person for you is just following what they’ve got to say, because it’s better to do that and make some progress than to be jumping around trying to triangulate off 50 different people.
You just end up doing nothing because there’s too much. The other thing, too, with the amount of information there is, it’s all very good and well to list them, in terms of listening to all this stuff, but you’ve actually got to implement it as well. Hours and hours of watching videos and not doing anything. It’s basically a year you’re wasting your time.
Action Over Endless Learning
It’s hours and hours of watching videos. There’s no step forward and stuff. I’ve been fortunate enough to visit New Zealand more years than I’m going to admit on camera, but I have visited New Zealand. I was able to go to the North and South Islands. Beautiful places. You’re on the North Island, correct? Up around Auckland and stuff.
Correct.
There are vast amounts of open space in New Zealand. Obviously, there are cities, Auckland, Wellington, Christchurch, where there are obviously more people. I’m just curious, what does real estate in New Zealand look like? Are there still huge tracts of land that, like, you can go out and buy 500, 600 hectares?
You can still definitely go and do that. There’s no shortage of large rural land here. The issue is that the cities are quiet. The cities or towns are quite dense, like Auckland, our biggest city. The North Island’s got about three-quarters of the population in it. The South Island has basically got Christchurch, which is the biggest city, followed by Dunedin, and small towns for the rest of it. It is very sparse. Our topography is all over the place. Trying to build anything, we’re trying to build a big city, it gets very difficult because you’re in the sea, you’re in a swamp, you’re on the side of a hill.
A lot of rock.
It’s not a huge amount of flat land anywhere either.
That’s true. What can you share about Auckland real estate? I’m just curious. I want you to talk a little about the Auckland real estate market. What might people like to know about it? Is it an easy market to get into? Maybe there are people here in the United States who are like, “I’m out of here, and I want to go to New Zealand.”
You’re out of there, and you want to go to New Zealand. You’re probably heading to Queenstown or somewhere like that. It’s more likely than Auckland, I would say. I mean, the Auckland market generally tends to lead everything that happens in New Zealand. If it happens in Auckland, it happens every six months. At the moment, cash flow and yield in Auckland just do not happen. They sit between 3% and 5% from a yield perspective.
They’re fairly low. Being the main population base, when things get cranking, Auckland tends to crank up first. The median house price there is, I cannot quite put it off the top of my head, but it’s close to sort of $800,000 for the median price. I think that the other thing with New Zealanders is that real estate is not cheap. It’s quite expensive in terms of what we earn compared to the price. Most of the stuff that we do is in regional New Zealand, and in our regional towns, populations range from 40,000 people to 90,000. They’re probably where regional towns sit.
Tune out the endless noise. Pick one trusted voice, apply the lessons, and stop triangulating fifty different opinions.
As I say, there’s growth in this, but we tend to move as a country as a whole. If one thing goes down, everything goes down. If one thing goes up, everything goes up. As opposed to even over in Australia, where they have the different states move at different rates, but their population’s four times the size of ours as well. Us sitting down here, there are five million people across a thousand miles in terms of length, is where we’re sitting at the moment.
It’s always interesting. I could say, obviously, the United States is enormous, and there are obviously huge swings here in the Bay Area. As I said, some of the prices are just ridiculous. Literally, I know of a house that just accepted an offer for over $4 million. This is not, in my opinion, that it’s a bad house, but that’s not what I mean. If I were dropping $4 million, I would think $4 million would get me. Yet, I could go to Detroit, and I might be able to buy a whole- literally. You said your median house price is $800,000, right?
I could buy one or possibly two whole blocks, depending on where I am in Detroit. There are places where you could buy something incredible, like a huge amount of property. You may have to put money into fixing them up and stuff. Now I did a little research, as I do with my guests. Talk a little about what you do and what your company does. They’re helping people. Is it more on the real estate investment side, so investment properties?
In terms of our company, we represent buyers. We do not sell anything. That came from my time when I bought the farm, when we didn’t have great representation in terms of the decisions that we made. When I started reinvesting again in 2016, I went out to the market and saw there was a heap of people who really just had no idea about what they were doing. They think, “We’re going to go in and purchase some real estate.
I’ll talk to my mom, I’ll talk to my dad, I’ll talk to my drunk uncle at the barbecue, and hope that we’ve got hope that I get the right advice.” People turn up to open homes, and the real estate agent asks them what their budget is, and they tell them $300,000 at the time. You’d stand there and scratch your head and just go, “What are you guys doing? They’re not your friend. The selling agent is not there to help you out. They need to get the most out of the vendor.”
Between that and also having some friends that were in the UK that had, they used to them, or they called them sourcing agents over there. We saw the opportunity to start our company. From there, we didn’t do a whole lot in the first three or four years. 2020, 2021, it just happened to be around COVID time. We decided, “Look, I’m going to go out on my own rather than work for someone else.”
It took a little bit of time to get the wheels moving, but it was in 2020, 2022, and 2023 that I started taking it seriously, more seriously. We’ve also got project management. Any of our clients who are looking to purchase investment properties, they want to get them renovated. We look after that process for them as well. Also, the property management on the back end of that, too.
That is great to help the buyers. Again, I know the first time I went to buy a house, luckily, I had a really great real estate agent who, first of all, listened to what we were looking for and didn’t show us properties that did not fit what we were looking for, right? Nothing drives me up the wall more than when you say, “Here’s my budget,” and they show you a house that’s $100,000 over what you said you’re looking for. It’s a great house, but I simply cannot float that. That’s not going to work.
Be honest about your starting budget. Smart real estate investing begins by matching expectations to reality.
Years ago, I had my real estate license in Massachusetts. I was doing just like rentals and stuff. Again, with a little understanding of what the agent side was, and said, “First, let me help my client. Let me set realistic expectations of what they can and cannot get.” When I was doing the rental stuff, there were people I’d go, “What are you looking for?” They’d have this laundry list of things. I’m like, “At the budget that you have, you’re not going to get those things. They simply do not exist.”
Aligning Budget With Reality
We call it champagne taste on a bare budget.
They’re absolutely. Look, it’s great to have the champagne taste, but you have to be realistic that here’s what you’re going to go, “I want 5,000 square feet and six bedrooms, and I have $300,000.” “I’m not going to be able to help you because you’re not going to get that.” If we do, you’re going to need another $200,000 because the thing is about to fall over. It costs that little because it needs a lot of work.
It’s phenomenal how it changes over time, and you meet some really interesting people.
That’s interesting.
Walks of life and the ability to be able to go and help people progress along the pathway. There’s definitely some upside to that.
Definitely. Hadley, this has been great. If people just want more education, because I know you’re obviously talking specifically about the Auckland area, real estate, but I think you have information that’s applicable to everyone everywhere. How can they find you? How can they learn more from you?
The best place for us is on Instagram @HadleyNightingale. We’ve got our website, NewZealandPropertyBuyers.com. Instagram’s the place where we shoot most of our content.
Cool. I want to thank you so much for coming on. Really interesting conversation. I was looking forward to this conversation for a couple of months when we set it up. Thank you so much for getting up really early to be able to join me.
I appreciate it, Zander. Thanks so much.
No problem. I want to remind everyone that if you’re ready to begin your Epic journey, go to EpicBegins.com. I want to let you know I’m planning an event, a live Epic event. Coming up on January 23, 2027, in the San Francisco Bay Area. Go to Epic-Reset to find out more about that. As always, remember. Choices lead to the epic life that you want.
Important Links
About Hadley Nightingale
Hadley Nightingale is the CEO of New Zealand Property Buyers, founded in 2020. In five years, NZPB has helped 100+ clients secure investment properties across New Zealand and scaled from a two-person operation to a team of 13, operating remotely across New Zealand and Southeast Asia.
Hadley sits at the intersection of property and business. He talks to property investors who want to build wealth without the costly mistakes, and to business owners who want to scale without it consuming their life. He’s done both, and he’s built the systems to prove it. NZPB is an end-to-end buyers’ agency built for busy professionals and investors.
From acquisition through to renovation management, compliance, and ongoing property management, Hadley and his team handle the entire process so clients can invest with confidence.