April 10, 2023

JF3140: How to Overcome Analysis Paralysis in Real Estate Investing ft. Alyssa Holbrook



Alyssa Holbrook is a master certified life coach, helping real estate investors grow and shape their portfolios. After investing in her first rental property at 14 years old, Alyssa caught the bug for investing and has dedicated her life to helping others find success. In this episode, she talks about the biggest mindset hurdles facing new and experienced investors, how investors know they need a mindset coach, and how to find the right one for them.

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Alyssa Holbrook | Real Estate Background


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Ash Patel: Hello, Best Ever listeners. Welcome to the best real estate investing advice ever show. I'm Ash Patel and I'm with our guest today, Alyssa Holbrook. Alyssa is joining us from...

Alyssa Holbrook: Orlando, Florida.

Ash Patel: Orlando, Florida. She's a master certified life coach, and a master certified deep-dive coach. Alyssa helps investors grow and shape their portfolios. She bought her first rental property at 14 years old. Alyssa, welcome to the show, and thank you for your time today.

Alyssa Holbrook: Thank you so much for having me, Ash.

Ash Patel: It's our pleasure. Before we get started, can you give the Best Ever listeners a little bit more about your background and what you're focused on now?

Alyssa Holbrook: Sure. So I started investing at 14 years old, when I read Rich Dad, Poor Dad, and I had already had the entrepreneurial gene, so I started saving up my money. I thought that I would buy something ,else like a camera. And once I made $1,000, I was like "No way. If I can make this money make money for me, I'm going to do that."

Ash Patel: At 14 years old you had the wherewithal. What was your first purchase?

Alyssa Holbrook: It was a mobile home that was completely dilapidated, didn't work at all, and I was able to borrow $1,000 from my parents to fix it up, and then rent it out, and start making money from there.

Ash Patel: How did your parents not talked you out of buying a mobile home at 14? You said they supported you?

Alyssa Holbrook: They did. So my dad understood real estate, and he understood those principles, though they hadn't personally bought any investment properties yet... So I got to be the guinea pig and go first.

Ash Patel: And what was that experience like, and what did you do next?

Alyssa Holbrook: So that experience for me was really eye-opening. I think investing so young, I had no idea anything could go wrong, that I could lose money. I just started growing the money, and I bought a second mobile home and I remodeled it myself.

Ash Patel: And you were in junior high, or high school.

Alyssa Holbrook: I was in high school by then, so I could drive...

Ash Patel: Did you have help in doing all this, or did you take this all on yourself?

Alyssa Holbrook: Yeah, the remodeling and everything was just me; the mobile home park manager's daughter was able to come help me lay carpet. So we were just hammering carpet with our 90-pound girls...

Ash Patel: And Alyssa, you are a master certified life coach and a deep-dive coach. What does that mean?

Alyssa Holbrook: From the master certified coaching perspective, I'm able to understand people's mindsets and what helps them take larger action, and get to their goals a lot more quickly, and what's holding them back. So I'm trained specifically on seeing that part.

Ash Patel: Who's your target client?

Alyssa Holbrook: Someone who has about $100,000 to invest, and wants to get into real estate investing, but doesn't yet quite understand how that process works.

Ash Patel: Do you take people like me, that have been doing this for 10 years, and still have a lot of mindset struggles?

Alyssa Holbrook: Absolutely. Yeah.

Ash Patel: Okay. What is the biggest hurdle that people have to overcome with mindset when they're starting out?

Alyssa Holbrook: I would say it's just being willing to take action, because a lot of them get stuck in analysis paralysis. So you have so many options, and they don't know which one to choose.

Ash Patel: How do you help them overcome that? Is there a process where there's some analysis involved?

Alyssa Holbrook: Absolutely, yeah. We look at their overall goals that they want to create, the portfolio that they want to create, the outcomes in terms of cash flow, and then we dissect it from there, starting with very specific outcomes, and very specific next steps for them to make the decision.

Ash Patel: Are they younger people, older people, a mix?

Alyssa Holbrook: A mix. Most of people who find me have 10 years until they want to retire, and are thinking about that... So that works well.

Ash Patel: And how bad is that starting line for them? Do they already have capital, or do you deal with people that don't have a lot of net worth, and want to retire in 10 years?

Alyssa Holbrook: Generally, I'm working with entrepreneurs and small business owners who do have capital to begin with.

Ash Patel: Okay. In terms of mindset, for people that are more experienced in real estate, what's the biggest challenge that they have to overcome? So experienced people like me, right? I've been doing this for over 10 years, I've learned a lot of hard mindset lessons... What are ones that you help people that are experienced overcome, most commonly?

Alyssa Holbrook: It's usually that they aren't thinking big enough; that they're doing what has worked in the past, and that that seems enough for them. But what I find is that people have this desire to understand what their capacity is; what is possible for them. That was something I experienced early on, where I was playing the cashflow game, and I realized, "Okay, this isn't about doing enough", it was "How big could I possibly go?" Even as a 12-year old, I think I was like "Can I have $200 million of real estate?" I already had these big dreams.

Ash Patel: I could have used her help a lot over the years. So I get that going bigger part. Do you recommend people work together with partners, or is it going solo the whole route, is that okay?

Alyssa Holbrook: Yeah, most of the time the people that I'm working with want to start investing just themselves. So these people love control, and they love being able to figure it out. They have a lot of faith in themselves as solopreneurs, as entrepreneurs, that they can figure it out if things aren't working. So they like to be able to get in, get out when they want.

Ash Patel: Do you ever recommend that they partner up with people to go further, faster?

Alyssa Holbrook: Sure. If you want to do a JV, I can totally help you with that. They do that often.

Ash Patel: Now, let's deep-dive into - I'm an individual, I want to retire in 10 years; how much money do I have to start with?

Alyssa Holbrook: $100,000.

Ash Patel: I have $100,000. I want to retire in 10 years? What's my plan?

Alyssa Holbrook: So generally, it's going to be investing in multifamily. We try and get over four-units or at four-units. That's a pretty sweet spot if you have that amount of cash. And then also some smaller commercial is an option.

Ash Patel: Okay, and how actively involved am I in these deals? Or are they passive?

Alyssa Holbrook: You're actively involved. So that's part of it, is just having them become the investor who can invest over and over again... So you want to understand beginning to end; that's really important, because you can outsource it later, but you definitely want that ownership and that full understanding.

Ash Patel: Alright, so you're really teaching people how to become real estate investors?

Alyssa Holbrook: Yes. A lot of it is about what questions to ask; when you look at a property, can you see what no other investor sees? Can you look at it from a different angle, that's more creative? I always call it "solving for profit". We're going to solve for profit. If we can get that property's highest and best use, it's going to be incredible for everyone involved.

Ash Patel: Can you share with the Best Ever listeners a good example of solving for profit, where a client saw something out of the box that worked?

Alyssa Holbrook: I'll give an example of from our experience, because I just love it... So we were investing in some land; we found an off market deal, and then we could see that we could split this land up, sell one part to one builder, sell the other part to the other builder, keep a lot for ourself, and then negotiate with the builder to build us a fourplex at cost. So we put in 220k, made 320k, pledged 100k of that 320k as the downpayment, and then now we'll have recurring revenue, and we got our money out.

Ash Patel: How about an example of a failure where a client failed, just gave up, or something didn't work out?

Alyssa Holbrook: So this just barely happened with a cafe that one of my clients had made an offer on. We got it at a really great deal, very deep discount, but when we started getting into the numbers and into the due diligence, we could see that a lot was there that wasn't good. So we saw that the owner of the cafe had put his energy into a different business, in a different area... And just kind of picked up on that, and we're understanding that this isn't going to be a good investment for her to move forward on. And it's really important that you're able to take the emotion out of it, not think about those sunk costs, and just realize "I need to do the best thing for my investment portfolio overall."

Break: [00:08:59.12]

Ash Patel: I've gotta understand this... You will advise clients on different asset classes, as well as businesses. Where does your knowledge come from?

Alyssa Holbrook: So a lot of it is just from personal experience. I haven't been super-connected to all the gurus, but I've learned from my dad, who's been boots on the ground, watching deals go by for 32 years in this specific market. So understanding and watching the deals that other people got, there was often this feeling of like, "Oh, I would have bought it for that." That gives you more creativity; that gives me a lot more insights of what they could do.

Ash Patel: What's something that you find you have to push yourself and get yourelf out of a comfort zone in?

Alyssa Holbrook: Doing anything public. For me to write copy on my Instagram or something requires me leaving my comfort zone a lot. For me, making offers sometimes feels that way... But it's also kind of exciting, because you can structure it in a way that you can get out of that deal if needs be.

Ash Patel: What gives you anxiety or pause on making offerings? Is it the fact that it might go through, the fact that it might not go through? What is it about that?

Alyssa Holbrook: I think it's one of the negotiation between what's the number to come in at that won't be offensive, but will create a good deal.

Ash Patel: You don't want to hurt anybody's feelings?

Alyssa Holbrook: Yes, 100%.

Ash Patel: Alyssa, on your Instagram, we've seen something about "An offer is a handshake." Can you tell us about that?

Alyssa Holbrook: I see that investors get stuck in the deal analysis phase. So they look at a lot of different deals in their market, of the right type of property... And overall in the market, they tend to be kind of a similar cap rate and a similar return. So oftentimes we need to go in with a lower offer, and people get stuck in that analysis paralysis. So if we can get from thinking about making an offer to actually just doing it, that's the philosophy of "An offer is a handshake." It's not like we're committing to marry. It's just like, "I'm gonna shake your hand, we're gonna see if this will work, and get it moving."

Ash Patel: You started real estate investing at 14 years old. Are you still actively taking down deals?

Alyssa Holbrook: Yes.

Ash Patel: What's your latest deal?

Alyssa Holbrook: The latest deal was a doctor's office. The doctor wanted to stay, and he wanted to do a sale leaseback, so he wanted to cash out the money. Because of that, there was a discount from what a typical owner-occupant would pay to come in as an investor. So that really worked well for us. We actually ended up giving him two options. In our LOI we said "You could take this option with a lower lease, or this option with a higher lease", and the price was correlated.

Ash Patel: What is one thing you wish you did differently?

Alyssa Holbrook: On that deal, or on any deal?

Ash Patel: No, from the point that you started, maybe earlier in your career. What do you wish you had done differently?

Alyssa Holbrook: So I can think of a deal-specific answer to that question, which is - we did a development, and in the development we didn't think ahead to everything that could happen along the way, that could go wrong. So that's something I teach, is obstacles and strategies. So if you can anticipate, thinking -- it's called strategic pessimism, where we consider "This could happen, that could happen", and then you anticipate it ahead of time, and that becomes your strategy for how to take down the property.

Ash Patel: Alright, so you push your clients to go bigger. What are you doing to go bigger?

Alyssa Holbrook: For me, that is just continuing to explore different asset classes and different types of properties, rather than staying to one thing. So it creates a lot of diversity and a lot of experience.

Ash Patel: How do clients know that they need a mindset coach? Because we're often trapped in our own thoughts, and we're in a comfort zone. Like me, for years, I thought between $300,000 and $800,000 was the sweet spot, because I was afraid to go bigger, for a number of reasons; afraid of the risk, afraid I would fail... Now, looking back, I know I should have asked for a mentor, I should have asked for help... And I didn't. So how do people know that they need to get out of their own way and ask for help?

Alyssa Holbrook: If they're not making as much money as they want to make, or if their portfolio is not growing as fast as they want it to be growing, that's a really good indicator. I would also say for a lot of my clients it's just a feeling that they have, that they feel blocked, or they feel stuck, and they're not sure how to get through that block.

Ash Patel: There's a lot of mindset coaches out there; how does somebody find the right coach for them?

Alyssa Holbrook: So it's understanding different mindset coaches are certified in different ways. They're doing different things. So you want to make sure that the outcome that you want - that they'll push you in that way.

Ash Patel: And you are a certified life coach. Do you help them with things other than real estate? Do you help them with relationships, kids, and just life in general?

Alyssa Holbrook: Some of that comes up, but we really pay attention to it in relation to their investing. So if it's holding you back from investing, like for instance I have an investor who his kids are taking snow days; he stays home with them, and his spouse who has the nine to five job, they prioritize her work. And so there's a lot of mindset behind that, of what are you believing about your work, just because it's not as quick of a paid off, or maybe it is, but you're creating that, and you're holding yourself back from your success because of how you have this setup. So we now need to renegotiate that whole relationship because of that.

Ash Patel: Interesting. What is your best real estate investing advice ever?

Alyssa Holbrook: Definitely my dad talking with me and saying to start young; it's just a function of time, a lot of it. And we know that with appreciation, and interest rates, and everything; with inflation... That properties are going to become worth more over time.

Ash Patel: Alyssa, we're heading into March of 2023. We've got interest rates up, deals are harder to find... What do you tell people who are facing those economic headwinds, and just are down and out, because there's no good deals out there? They can't get sellers down, financing is killing deals... What's your advice to them?

Alyssa Holbrook: Well, it's interesting that you might be looking at it that way, because it's also possible that you just haven't found that deal yet. So if you can get 15-20 no's and make it mean almost nothing, then you're gonna get a yes sooner. So it's reinterpreting what that no means and what you're making it mean about the market, about you, about how you're making offers.

Ash Patel: I love it. Alyssa, are you ready for the Best Ever Lightning Round?

Alyssa Holbrook: Yes.

Ash Patel: Alright. That wasn't a confident. Are you ready?!

Alyssa Holbrook: I'm ready!

Ash Patel: Alright, Alyssa, what's the Best Ever book you recently read?

Alyssa Holbrook: I would say Emerging Markets.

Ash Patel: What was your big takeaway from that?

Alyssa Holbrook: That you can compress what a property would become worth usually over 10 years, with appreciation you can compress it down to three, by understanding micro markets, and markets just within local markets.

Ash Patel: Alyssa, what's the Best Ever way you like to give back?

Alyssa Holbrook: I love talking with new investors, just because it's so fun to understand and to show them what's possible, and how much can happen in a short amount of time. So that's fun.

Ash Patel: And Alyssa, how can the Best Ever listeners get a hold of you?

Alyssa Holbrook: You can go to AlyssaHolbrook.as.me/consultcall, and just book a call with me. I'm so happy to talk with you.

Ash Patel: Alyssa, I wish I had booked a call with you 10 years ago when I started... But thank you for taking the time out of your day, sharing what it means to be a life mindset coach, and really how that applies to real estate. I think it's really important that a lot of us learn these lessons earlier on, and shorten that learning curve. So thank you again for your time.

Alyssa Holbrook: Thank you so much, Ash.

Ash Patel: Best Ever listeners, thank you for joining us. If you enjoyed this episode, please leave us a five star review. Share this podcast with somebody you think can benefit from it. Also follow, subscribe, and have a Best Ever day.

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