6 Big Lessons from 1,000+ Property Questions

30 Oct 2025 · 26 min · 9 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

The hosts review patterns from answering 1,000+ listener property questions on “Ask Rob and Rob,” then share six “big lessons” about investing mindset and decision-making. They also announce a new AI tool trained on their content to answer questions instantly.

Guest backgrounds

No guests. Two hosts, Rob and Rob (Property Podcast), who buy £100m+ of property annually for clients and run “Ask Rob and Rob.”

Key claims

Most questions are driven by emotion and need reassurance/permission to act, not lack of facts. Investors over-focus on tactics (mortgages/areas/company setup) and under-focus on strategy (“why invest?”). Market timing obsession and waiting for “perfect” moments causes missed opportunities; deals can be best when uncertainty is high. Limited company questions are often a stalling mechanism; location analysis has become more important as investors diversify geographically. “You never feel ready,” but big-picture strategy helps.

Notable examples

Renters’ Rights Bill (royal assent; waiting for implementation timeline; indefinite tenancies; Section 21). Market timing example: buying near the 2007 peak led to temporary paper losses but later recovery.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Emerging Lessons from 1,000 Questions

0:45 to 3:08

The hosts discuss the patterns and lessons learned from answering over a thousand listener questions.

“But we also answer your questions on Ask Rob and Rob every week.”

The Emotional Landscape of Property Investment

3:08 to 5:30

Exploration of the emotional aspects tied to property investment and the reassurance sought by investors.

“It's been super valuable, Rob, for us looking back and extracting these lessons.”

The Importance of Strategy Over Tactics

5:30 to 6:52

Discussion on why strategic thinking should precede tactical decisions in property investment.

“So having the opportunity to call in and get that reassurance, I think it's been really powerful.”

Overcoming Procrastination and Market Timing

6:52 to 11:20

Hosts address the challenges of market timing and the tendency to procrastinate instead of investing.

“Strategy is what's going to create the wealth.”

Common Questions from Property Investors

11:20 to 14:00

The hosts reveal the most frequently asked questions from their listeners regarding property investment.

“And we've been doing this over 10 years now saying that the market's about to crash.”

Hindsight vs. Action

14:00 to 14:37

Understanding the challenge of making timely investment decisions.

“So would it have been better if they'd waited a couple of years?”

The Limited Company Question

14:37 to 18:15

Exploring the most asked question about buying property through limited companies.

“limited companies and buying property through them we get questions in pretty much every week unlimited companies?”

The Importance of Location

18:15 to 19:36

Discussing the shifting trends in investment locations over the last decade.

“we are now getting more questions about location than ever.”

Overcoming Fear and Imposter Syndrome

19:36 to 22:01

Addressing common fears and questions that hinder potential investors.

“And lesson number six is you never feel ready.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:02Hi, I'm Rob. And I'm Rob. No, no, no, this is not Ask Rob and Rob, but we are borrowing from Ask Rob and Rob because we have answered over a thousand of your questions now on Ask Rob and Rob, and it's been a privilege. But what's more important for today's episode is we've noticed a pattern of questions that have emerged from answering all those questions. And what we've identified is six really valuable lessons from those files and questions. And we're going to share them with you today.

0:36Yes, welcome to The Property Podcast. Thank you for joining us. In case you don't know, we buy more than£100 million worth of property every year for our clients. You can find out about that at propertyhub.net slash invest. But we also answer your questions on Ask Rob and Rob every week. And we've answered a thousand of them now. So in this episode, we're going to share the big overall meta lessons that we've learned from answering all these questions will be super valuable for you. But make sure you stick around to the end because we're going to be revealing a whole new way that you can get your questions answered instantly.

1:04It's time for our new story that we can rob. I'm going to take you right into the centre of your fun zone because I'm giving you a new story where you can talk about the renter's rights bill because this headline reads the controversial renting reforms now just days away from becoming law rob it must be like christmas coming like this event you've been building it up for so long i don't know if you've bought a nice outfit for it or like how are you going to mark the occasion but and do you want to tell us what yeah yeah well this is a big moment because the rent is rights bill which we've been talking about for it feels like years because it has been years we've been talking about it for so long it finally is law it has had royal assent which means there is no more uncertainty, no more debating, no more things that might change.

1:48It is now set in stone. But the final important thing that we don't know, a really important thing, is when. So what we're waiting for, which should happen really soon, as in the next couple of weeks, is we should see the implementation timeline. So which bits of the new law are going to come into effect when. So there are bits of it, like the new landlord database, which are probably going to be quite a way off in the future because someone has to go away and build it. But the first part to come in is going to be the bit that we all really care about, which is this new type of tenancy, where tenancies are indefinite from the start and you can't bring them to an end using Section 21.

2:21There have been rumours of giving the industry three months to six months to prepare for that before it comes into effect, but this is what we're waiting to find out. So that's the final key piece of information. Once we know that, we will of course be covering it extensively on the podcast, telling you everything you need to know and everything you need to do in the build-up to that happening. so the title really lays out what this episode is we have answered over a thousand of your questions now on ask rob and rob and from answering those 1 000 questions we've seen as a clear pattern that's emerged and we wanted to put this pattern in front of you and this pattern of questions has forced us to think okay what are the most valuable things we can answer what are the six biggest lessons from these 1 000 questions and that's exactly what we're going to share with you today.

3:07So it's mega valuable. It's been super valuable, Rob, for us looking back and extracting these lessons. It has. And it's really interesting because the world is in a very different position from where it was 10 years ago in many ways. But in terms of access to information, when we started the podcast, there really weren't that many sources of information out there. You had your landlord associations, you had a couple of forums, but there wasn't much. Now we are flooded with information. But I wouldn't say that that has given anyone any more certainty because people are still asking the same questions that they were 10 years ago.

3:39But they're asking not so much about the facts, but what it means for them. And that's the kind of thing that we can get into on Ask Rob and Rob that you're not going to get from asking ChatGPT or whatever. And I think, Rob, that's another big theme. Yes, people ask technical questions, but behind that is usually emotion. There's a lot of emotion wrapped up in the questions that people ask. And that's understandable, right? Because property investment is kind of a big deal. It's not like you're putting 50 quid into this and hoping for the best. Many people are putting their life savings or a vast majority of their life savings on the line when they invest.

4:11And if they've not done this before, they can feel emotional about it. And property for all the way through can be emotional if you let it be. The emotion of getting your tenant in, it feeling like the absolute everything when it's your first property and you have a void for a few weeks and people start panicking. There's panic, there's joy let's not forget there is joy in this process as well when you make that investment you get that deal agreed there's so many ups and downs when it comes to property but that's because so much is at stake and people fear getting it wrong and that sometimes means that people are paralyzed from making decisions or moving forward so what a lot of these callers are looking for is they're looking for confidence and in a lot of cases i think that people know the answer already.

5:02The people asking these questions know the answer, but they just want somebody else to reassure them that what they're doing is the right thing, that they haven't lost the plot. Because becoming a property investor or building on your portfolio, it's not normal. Most people don't do this. So you are stepping out and away from the crowd. You're doing something that others fear doing or haven't put themselves in a position to be able to do yet. And that makes you an outlier. Being an outlier can be scary. So having the opportunity to call in and get that reassurance, I think it's been really powerful.

5:36Definitely. Powerful for the person asking, powerful for the people listening, and also for us. The other thing, looking back over all the questions we've answered, is how much we have learned. Because these questions have forced us to explore and research topics that we wouldn't otherwise have covered. And a lot of the time, they can be super niche. It's not the kind of thing that we're going to make a full episode about. But if someone's asked the question, the great thing is enough people listen to this show that if one person has asked it, there is no way that they are the only person where this question has crossed their mind.

6:04If one person has gone to the trouble of calling in, you can be sure that probably 50 people at least have had this question, even if it's in a pretty niche area of property. So the amount of variety that this show has had because of the questions that people have sent in has massively helped everyone. So a big thank you to you if you're one of those 1 ,000 questions, or one of the selects band, you've managed to have more than one question answered. because you've not just helped yourself, you've helped your fellow listeners and you've helped us keep learning as well. So that's what we noticed broadly from going back and looking at the questions and how they've changed over time.

6:31But there are also, as you said, Rob, six big lessons that we've taken away from doing this exercise, from going back and studying these questions that we think that everyone will benefit from hearing. Yeah, absolutely. And number one is a big one, is that people really focus on the tactics far too much. and at the cost of strategy. Strategy is the winner. Strategy is what's going to create the wealth. But people want to know what's the best mortgage? What is the best area to invest in right now? Or how should I structure my company? Yes, these things are all important and they are tactical decisions that you need to make.

7:13But what is far more important is starting out with the strategy and so few people do this. A real simple one is why am I investing? What outcome am I looking for? What does success look like if I go through this process of investing? That even though it is super important so few people do. They just don't go through that process and the why once you understand what the outcomes need to be for you for this to be a success this being property investment, you make better tactical decisions because you then start to be able to rule things in and out based on the bigger picture outcome. I think, Rob, the reason why people don't do this is it's much easier to focus on tactical stuff because the tactical stuff is the here and now.

8:03It's a yes, no. It's make a decision. It's ticking a box. Whereas going bigger, focus on your strategy requires time, thought and effort. it that's right that is the real hard thinking but once you do that then most of the tactical stuff answers itself so it is that lead domino but it's very unusual for people to do that if you listen to the questions that we answer how much of the time do we start by saying well it depends on what you want do we try to guess different things that the person might want and lay out different options based on that it's really unusual for someone to call in and say right this is what i want to do this is the situation i'm in here's where i am now here's where i want lesson.

8:42So many of these 1 ,000 questions answer themselves if you do just do that strategic thinking first. The second lesson that stood out to me, and you've already alluded to this, Rob, is that what people are often asking for is not so much knowledge, but almost permission. What they want is the confidence to act. So a lot of the time, people will lay out a situation and say, I've done the research, I've spoken to so-and-so, and I think this is what I should do. And then all we have to do is say, yeah, that's probably what you should do. So, linking back to the previous lesson, though, a lot of the time they don't say what it is that they want, so I have to caveat with that.

9:13But there's like, well, yeah, just go do the thing. That is so, so hard to do because it is really scary. You are committing a lot of money. You're at the early stages not diversifying. You're probably taking close to all of your funds and putting it into one particular deal or opportunity. And that's really scary. And you can definitely make the mistake of rushing in. We do see people making the mistake of being hasty, not really thinking it through, just doing it, and then it turns out to be the wrong thing to do. But far more often than that, we see people making the opposite mistake, which is endlessly waiting for the moment that they know everything, endlessly waiting for the perfect opportunity, where there's absolutely no niggles, no doubt at all, and it just doesn't happen.

9:54When I think about the people who have been with us over this 10 years plus that we've been doing the podcast, and there are people who've been listening that whole time, they write in occasionally and say, oh, I've just bought my third, I've just bought my fourth, I've just bought my fifth. the people who've done that most of the time they're just doing it they're not overthinking it and they're not going to get it right every time but the great thing about property is that time solves the majority of the mistakes that you've made in the end you're right rob and people are waiting for the perfect time in two senses i've noticed one is like the internal perfect so your immediate world so your life events so you might be waiting for this to play out before you move forward or a certain date i'm going to do it next year wherever it may be like you have these perfect moments that you try to establish internally and then the externals, the market, you're waiting for the perfect market to invest in.

10:43And if you want to find a reason both internally and externally not to invest, you will always find it. That's the great news if you like procrastinating. You're always going to find a reason not to move forward with your property portfolio and other big things in life, by the way. There's always a reason you can find not to do it. If you want to talk yourself out of the market right now, if you go back through history on online forums, YouTube comments, wherever, you will find people saying the market's about to crash. It amuses me now that since we started this podcast, how people have filled comment sections online year after year.

11:26And we've been doing this over 10 years now saying that the market's about to crash. You know what? They were always wrong. But if you were one of those people five years ago, procrastinated because you read those comments, you didn't move forward. You didn't win. There are people now saying, I'm going to wait for the budget. I'm going to wait for renters' rights to play out and see what happens there. You absolutely can. But right now, we're doing some of the best deals we've ever done in Prop2Up Invest. You know why? Because there is that uncertainty. And that's another lesson here that is not listed in the six.

11:57But actually, when things aren't great, it's a great time to invest. waiting for perfect is probably the worst time to invest because that's when everyone feels confident and when everyone feels confidence in property that's when you shouldn't be so take confidence from people's lack of confidence because that's probably when it's a better time to invest and the deals that you do in those environments absolutely show that and what i've just said really leads on and i've semi-covered the third lesson which is there's an obsession around market timing. People always want the best time. Is now the right time to invest?

12:35But the best time to invest was yesterday, Rob, or further into the past. The time to invest is when you get a time machine. It's always better to get going, but people are always waiting for that optimal moment, the best possible time to get going. Yeah, the second most frequent question, we'll tell you what the first most frequent is, the second most frequent question of the 1 ,000, has been, is it a good time to buy? Phrased in different ways, but it's what everyone wants to know and understand the fear of making a move at the wrong time. Especially because, as we've said, you're tying up a lot of money.

13:08You're probably tying up most of your funds. It'd be lovely if you could just drip feed into the market, but most people don't have the funds to do that. They just have to buy one property at a time when they can. That's what the vast, vast, vast majority of people do. So it is really scary. But when this comes up, we normally try to reassure people with data and go, well, what would have happened in the past if you had bought at a terrible time? What would have happened if you'd bought in 2007 at the absolute market peak? Where would that leave you? And the answer, when you go back and look at the data, is, well, yeah, if you buy in the 18 months just before a crash, it's normally the 18-month period where you get the real boom that you don't want to be buying.

13:42But if you do, then you'll end up with a paper loss for some period of time, but the rent will keep coming in. And some number of years later, you'll be back on paper ahead again. The people who did the absolute worst, craziest, badly timed, overpaying type deals in 2007 are back to being well ahead by now. So would it have been better if they'd waited a couple of years? Yeah, it would have been. They would have been even further ahead. But you just can't do that. You can do it with hindsight, but you can't act that way when you're having to look forward. Otherwise, you do end up in this position of just never doing anything because you never get that certainty.

14:15So that's a message that we have been banging away at and we will keep on doing that because it is the second most asked question but rob what is the most asked question out of the thousand well if you're listening guess now don't shout out on the tube because you look weird but if you are listening in your head guess okay here's the answer limited company should i buy through a limited company should i set up a limited company or any questions related to limited companies and buying property through them we get questions in pretty much every week unlimited companies? Now, we don't answer them every week because it'd make a pretty boring show if we did.

14:52The answer for most people is yes, but there are obviously nuances and that's not advice, that's just generalization. But what's really interesting is when you dig behind this, and we've touched on it a little bit already, but it's people asking, am I doing it the right way rather than just about tax? They're looking for that validation. They're just looking for that confidence to move forward. It's pretty simple to understand whether it's right or wrong for you to investor in a limited company. If you're residing in the UK and your circumstances are fairly normal, there's a good chance that it's the best way to operate.

15:22Again, though, I think this is important to note that some people are using this as a deliberate blocker to themselves. They won't see this. They won't observe their own behavior, but it's us observing them. And this is not everyone, but some people will be, oh, well, I can't go forward yet because I need to make sure I get this right. And I understand why, because tax is a big part of property investing or any investing but really it's an excuse it's a stalling mechanism to get going what's far more important as we've said is your strategy not the tactics and getting the strategy right this is a tactical thing that most people can solve in under an hour and if you're listening to this and you want a link to some tax advice we will put some links in the show notes of this episode if you still want that expert advice and you still are unsure but the point is it's a minor box ticking exercise that you need to go through for most people, but it's not the be-all and end-all.

16:17But if you reviewed all the questions that we get, people seem to think that it is the be-all and end-all. It is the biggest thing, and it really isn't. It's just something that you quickly need to solve, keep in quickly, and then move on with the important stuff, your strategy, the investing. This is just something that, in some circumstances, make people feel important because I'm setting up a company and I'm a professional investor. that might be it for some people as well but the truth is while it may feel big it really isn't it's not that important once you've set it up it's just something you do and then you get on to the really important stuff that's right and one of the important things is where you invest and this is something that we've seen a shift in over the last decade because this is the fifth lesson we've taken away from reviewing these questions location is a hotter topic than ever it's now an active decision for the vast majority of investors.

17:1110 plus years ago the default by far was that people would invest close to where they lived and given that a lot of investors a lot of people who listen to the show live in the southeast they would be investing in the southeast generally as close to home as they could and back then in some cases that made sense in some cases it didn't but it was what people defaulted to but then over time things shifted we've gradually gone to progression where there's been a massive divergence between the north and the south where london and the southeast are struggling manchester since about 2016 onwards has really boomed that has brought up the whole region there are other parts of the north and the midlands that have become fantastic places to invest not just in terms of the yield which was always stronger but in terms of the capital growth as well that's been a gradual process over the years to the point where it is now screamingly obvious it used to be the case that people were resistant to investing away from where they lived and completely understand why that's the case.

18:05But while that was an argument we used to have to make frequently when we're talking to people, it's really not anymore. Most people just accept it because it is so extremely obvious. And what that means is that we are now getting more questions about location than ever. Because when you go away from the default of, oh, well, invest as close to home as I can, then you can invest anywhere. And the UK can be a scarily big place. So we get loads of questions about what do you think of this area? What do you think of that area? You did say that you like this area. Do you still like this area? and then if we haven't mentioned a particular area people want to know why oh you included derby in your hot spots but you didn't mention this other place why does that mean it's not a good place to invest these questions come up all the time and we're happy that they do because they're interesting things to talk about and again if one person is thinking about an area and sending a question in then lots of people will be interested in the answer but more valuable than hearing our opinion on an area which is just an opinion it's far better to be able to come to your own opinion to have an actual process for understanding well what is it that makes somewhere a strong investment area what factors are we looking at when we do that and then you can just look at those same factors do that same analysis for any area that's of interest to you and we don't make a secret of that we've spoken about it on the podcast multiple times we've also written that process down so we've got a free toolkit it's got spreadsheets and deal calculators list of our hot spots a checklist for what to think about when it comes to the limited company question all that kind of stuff but it's also got our full process in there for how we analyze an area so if that is a question that you have.

19:28If you've got a location on your mind and you want to know whether it's somewhere you should think about investing or not, then go to the show notes, find the link to that toolkit completely free and follow that process. And lesson number six is you never feel ready. You don't. And often you'll feel imposter syndrome from even getting going, like who am I to be an investor or who am I to have a larger portfolio? There's doubt, there's fear, there's just that step that people have to take that is really difficult. But what is fantastic is we know that Ask Grump and Rob has been an enabler for many people, not just those who've asked the questions, but those who are listening to the questions and going, oh, I'm in that situation.

20:06It's not that big of a deal. I can move forward. I can do this. Fear will exist. Not feeling ready to get started will always exist. Having doubts about expanding your portfolio will always exist. These are things that play out, but that's okay. The reason why this is an important lesson is it's absolutely okay to feel that way. It is normal. Most people will feel it at some time or another. And if you are feeling it now, you're not alone. We've answered this question for many, many people. And we know that this is such a big thing. But as we've touched on already, it's the bigger picture that's more important.

20:43And that then helps you to move forward. that then helps you to be ready because when you've got the big why you understand why you want to do this and then you've got some strategy around it it makes these sometimes what feel like challenging decisions a lot easier and listen we're not going anywhere we're still here ask grob and rob is going to exist you've got chat to bt as well it's not quite as good as us yet but you know you've got these sounding boards there are people out there who can help you There are people who are investors already who are willing to help you. We'll keep answering questions.

21:19We'll keep using those questions as lessons for all of you to get that unlocked, to move you forward on the next step. But remember, it's amazing how many of these lessons, a lot of it is around emotion. A lot of it is the human side of property investment, which is great, right? It feels exciting as well. There are upsides to the emotions as well. But it's really interesting to observe that when we've gone back through these thousand questions that we've answered, how much emotion plays into this and how people are using Ask Rob and Rob because they're not quite ready yet. But actually, after listening to all these questions, answering all these questions and reviewing many more, most of you are ready.

21:58You just want that validation. And you know what? We'll keep giving you it. and rob the human part is important but our hub extra this week is non-human but i mean if you're going to go non-human it doesn't get any better than this i mean this is better than chat gbt this is the next level of human advancement i don't think we've ever had a better hub extra right build up a bit but i think in the context of this episode you were right because we are talking about rob and rob ai yes we have digitally cloned ourselves or rather we've cloned our brains It didn't take long. Well, you'd be surprised.

22:34There is a lot of information in there. What we've done is we've built an AI. It basically looks like ChatGPT. But rather than just having all that generic information, it's been specifically trained on a vast amount of our material from over the years. That's been trained on the information from all my books, been trained on podcast episodes, been trained on YouTube videos. So it specifically has all the knowledge that we've shared over the last decade plus. But more than that, it's been trained to think like we think. So it won't just tell you a factual answer. It will ask you the kind of questions that we would ask you if we were having this conversation in person.

23:05And it will give you opinions, perspectives that are the same as ours, because poor thing, it's been forced to study so much of our stuff. So this is something that we are really excited about, because as you'll know, we are huge advocates of AI. And now we have our own AI that you can use to get your questions answered. And although we haven't talked about this on the podcast before, we've been trialing it, we've been tweaking it, and we've had people say really great things about how it's helped them out and the quality of the answers, the quality of the conversations that they're having with it.

23:30So you can try this out now and get your questions answered. It's completely free. You can use it at propertyhub.net slash AI. But do please as well, keep on sending your questions in for Ask Rob and Rob, the podcast, because it'd be a real shame if virtual Rob and Rob got to have all the fun and the podcast just died. So do use it at propertyhub.net slash AI, but include us as well, please. I might see if it can do all the big questions for my kids as well, like where are my shin pads or what time Are we leaving? You know, all the big, deep questions that I get on a daily basis. We'll see. I mean, if it could do that, then I'm in a very good place.

24:02I'll test it. I'll see. Okay, that's us done for the end of the week. Thank you for joining us for this special episode. I hope you've got benefit from it. And if you have, please share what we do. We want to help as many people as possible. We keep building stuff for free. We keep putting out content for free. Yes, we have a business that a few of you work with, but tens of thousands of you don't, and that's amazing. and we just want to keep pushing all this stuff out there as much as we can and if you haven't got somebody you can refer us to then leave a nice review somewhere you know we do read them we like them we appreciate them and hopefully you appreciate the stuff we keep putting out because we're going to keep doing it thanks everyone take care have fun bye-bye bye-bye

From the publisher

We’ve answered over 1,000 of your questions since our first Ask Rob & Rob episode - and six clear themes have emerged.  

In this episode, we’re breaking down the key lessons behind those questions to share the most valuable insights you can apply to your own property journey. 

 

Keep your finger on the pulse with the FREE Property Pulse newsletter. 

(1:03) News story of the week

(6:41) Lesson 1

(8:48) Lesson 2

(12:21) Lesson 3

(14:23) Lesson 4

(16:55) Lesson 5

(19:36) Lesson 6

(22:02) Hub Extra 

Links mentioned: 

Check out tax experts Provestor for advice or email them directly at hello@provestor.co.uk

Access our location guide & limited company tools here

Ask Rob AI a question 

Enjoy the show? 

Leave us a review on Apple Podcasts - it really helps others find us!

Sign up for our free weekly newsletter, Property Pulse

Find out more about Property Hub Invest

More from The Property Podcast

All 131 episodes
6 Big Lessons from 1,000+ Property QuestionsThe Property Podcast · 26 min
Listen in VO