In short
Episode topic: Solo episode where Natalie Palmer (Airbnb ambassador, 17-time superhost, 1,000+ reservations) explains her first real estate investor capital raise for an upstate New York STR project (“For the Love of Upstate,” linked to the Pearson House story). She covers the deal timeline, what she did right/wrong, investor psychology, missed deadlines, and lessons for future raises.
Guest backgrounds
No guests; only Natalie.
Key claims
- She declined partnering on the Pearson House initially due to fear of being a “guinea pig,” later regretting it.
- She raised capital after getting investor interest from her audience and after Maddie Johnson’s capital-raiser stopped working with them.
- She secured the property under contract first, then raised investors (to accurately underwrite returns and handle DSCR/escrow variables).
- Biggest mistake: setting a minimum investment too high (initially ~120k; crickets) and including an overwhelming pro forma in the first pitch email.
- Fixes: lowered minimum to $50k and sent a Loom video walkthrough of the pro forma, which she says closed 5 of 8 investors.
- She intentionally turned away 3 investors whose goals didn’t match the 7-year hold/repayment structure.
Notable examples
- Timeline: started pitching May 1; last investor wired July 30; closed after extending escrow when she missed an initial bank deadline.
- Deadline recovery: paid the seller ~$3,500/month (more than a ~$3,000 mortgage) to cover the extra month.
- Investor psychology: first signed partner triggered “domino” commitments within 48 hours.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOCareer Shift Announcement
0:28 to 1:00
Natalie shares a major career pivot into raising capital for real estate.
“If that sounds good to you, let's get right into the show.”
Outline of Today's Episode
1:00 to 2:04
Overview of what will be discussed, including lessons learned in raising capital.
“I haven't really posted much on social media lately because, I mean, no real reason.”
Backstory on Investor Partners
2:04 to 3:08
Natalie shares her journey and the connections that led to her first investment project.
“things I've ever done in my professional career.”
Regrets and Missed Opportunities
3:08 to 5:54
Natalie reflects on past investment opportunities and her regrets about not participating.
“Let me reference this outline here because as you guys know, I will talk and talk and talk and I will lose my train of thought.”
Building Trust with the Audience
5:54 to 8:04
Discussion on trust built with listeners and interest in investing in short-term rentals.
“really just admired the whole formula that they came up with to make these properties in upstate New York, absolutely kick ass.”
The Catalyst for Change
8:04 to 9:35
How a conference conversation sparked the decision to raise capital.
“Like, I don't know the first thing about this.”
Sponsor Introduction
9:35 to 10:00
Introduction of the podcast's sponsor, Logify.
“So it ended up being, I want to say like four weeks later, she texts me end of April and she's like, all right, we're under contract.”
Pitching Investors
10:24 to 11:01
Natalie discusses the timeline and process of securing investor capital for her project.
“Just hit the link in the show notes to get started.”
The Importance of Timing in Raising Capital
11:01 to 14:00
Explaining the strategy of securing property before investors and the rationale behind it.
“So pretty much three months, just under three months, shy of a day, it took to secure the capital for this whole project.”
Understanding Property Regulations and Capital Raising
14:00 to 15:06
Learn about key property regulations and the order of raising capital.
“in the know of how the whole structure worked, what we were going for, what kind of income we were able to make.”
Show all 26 chapters
Navigating Fundraising Timelines and Deadlines
15:06 to 18:27
Explore the importance of fundraising deadlines and the loan application process.
“and then we find the deal or how does that work?”
The Pressure of Securing Initial Investors
18:27 to 20:39
Discover the psychological factors influencing initial investor commitments.
“The next three people, those other three people that were already interested and were just skeptical because no one had signed on, they all committed within like the next 48 hours.”
Building Confidence in Fundraising Efforts
20:39 to 22:35
Learn how initial successes can change your approach to fundraising.
“You guys know that the bank, that deadline was like a very formal thing.”
Adjusting Investment Minimums for Better Response
22:35 to 26:24
Find out how lowering investment thresholds can improve investor engagement.
“Now, let me tell you guys one of the big mistakes that I made starting with this deal.”
Handling Mistakes and Delays in Capital Raising
26:24 to 28:01
Understand how to address issues that arise during fundraising and negotiations.
“So we did have some time on our hands, but basically the first month was just gone from kind of like us figuring out the right amount and how to target these people.”
Dealing with Missed Deadlines
28:01 to 29:56
Learn how to handle missed deadlines in capital raising.
“But I want to tell you guys, if this happens to you, it is not the end of the world.”
Initial Pitch Mistakes
29:57 to 32:44
Discover common mistakes in initial investor pitches and how to avoid them.
“have to carry two mortgage payments at the same time.”
Improving Investor Communication
32:45 to 39:22
Understand the importance of clear communication and video explanations for investors.
“everyone I had emailed, the response rate was not what I wanted it to be.”
Strategies for Successful Capital Raising
39:23 to 42:04
Explore effective strategies and terms for raising capital successfully.
“So that was a huge thing that I will be changing for next time that I'm pitching people.”
Generous Investor Terms and Lessons from 'The Purple Cow'
42:04 to 44:10
Learn how generous terms for investors can set your capital raise apart.
“them 100 % of profits until they're paid back.”
Choosing the Right Investors for Success
44:11 to 47:40
Discover the importance of selecting investors that align with your vision.
“when I told her, I don't think that you need to provide all of this.”
Building Trust and Relationships in Capital Raising
47:41 to 51:38
Understand how building relationships fosters trust and confidence in deals.
“Like having people that were like wanting to work with us and just not being able to be flexible on the terms like did I do the wrong thing.”
Finding Joy and Fulfillment in Capital Raising
51:39 to 55:08
Explore the rewarding experience of raising capital and the joy of success.
“And I just loved having these conversations and getting to know these partners and having these relationships.”
Celebrating Milestones in Capital Raising
55:09 to 56:00
Learn about the emotional journey and excitement of securing investor trust.
“They're already submitting offerings out there.”
The Thrill of Raising Capital
56:00 to 57:24
Learn about the emotional highs and fulfillment of successfully securing capital for a project.
“Obviously, I didn't get$100 ,000 that's going towards the deal and everything.”
Essential Tools for Investors
57:24 to 58:07
Discover the importance of creating a form to gather potential investor information and goals.
“Like I said, I will link the form that I had made below.”
Transcript
Automatic transcript. May contain errors.0:00Natalie Palmer:Hello, welcome, and thanks for checking in today to No Vacancy, the podcast. I'm your host, Natalie Palmer. I'm an Airbnb ambassador and 17-time superhost, and I've hosted over 1 ,000 reservations. I'm a stay-at-home mom of two and manage my eight listings remotely. My mission is to help new and experienced vacation rental hosts turn their listings into fully booked, profitable properties that can be managed from anywhere so you too can have no vacancies. If that sounds good to you, let's get right into the show.
0:52Hello, everybody, and welcome back to another episode of No Vacancy, the podcast. I'm your host, Natalie Palmer.
0:57Natalie Palmer:Today we have no guest on. It is just me for a solo episode, catching up with you guys and letting you know about a pretty major pivot career shift, whatever you want to call it, that's been going on behind the scenes for the last few months. I haven't really posted much on social media lately because, I mean, no real reason. I've just been really enjoying my summer and haven't been opening Instagram at all, which has been lovely. but if you're on my email list you would have gotten a few updates about this but essentially I have made the decision this was back in May slash June but I made the decision to close the doors on my coaching program and go all in on raising capital for real estate projects and I get to officially announce that the first project I raised investor capital for is officially 100 % funded.
1:57Natalie Palmer:Oh, that is so cool to say. Maybe this feeling will wear off once I've done a few projects. But as of right now, I seriously think that this is one of the coolest things I've ever done in my professional career. I can't get over it. So I'm going to walk you guys through. Gosh, we have so much to catch up on. Okay, I actually made an outline for this episode because I knew that I would start to ramble and lose my train of thought. So this is what's in my outline. This is what we're going to go through today. I'm going to walk you guys through this deal, through the process of my first time raising capital, the backstory of this deal, how I found the partners.
2:32Natalie Palmer:I'm going to break down the timeline of raising investor capital and the timeline of closing. There was so much I learned in that process. I'm going to just be very open and share everything that I did wrong with trying to secure investors and everything that I did right. I also learned so much about the psychology of investors and partners. I'm going to break all of that down for you guys. Going to go through some regrets I've had with all of this and the decision to close my coaching program. And then we'll close off today with me telling you guys what's next and what I'll be working on next.
3:08Natalie Palmer:So without further ado, let's dive in. Let me reference this outline here because as you guys know, I will talk and talk and talk and I will lose my train of thought. Okay, so here we go. So we just closed on a property. Oh, this is so exciting. So quick backstory, and I'm going to link the episode that I did with Maddie Johnson. Gosh, when was that already a couple months ago at this point, I will link that in the show notes, because that's who I worked with to raise investor capital. So if you guys want to go back and sort of listen to more of the details on the deal, you can go listen to that episode.
3:41But essentially, quick backstory is if any of you follow Skylar and Maddie on Instagram, I have been friends with them for years at this point. And yeah, we've just always supported each other in what we're doing.
3:54Natalie Palmer:They used to be investors in Big Bear. So we connected a lot back in the day there. And then a couple of years ago, they made the call to move to upstate New York and start building a portfolio there. And this is so full circle, but the very first property that they ever wanted investor capital for the Pearson house. And again, if you guys follow them on Instagram or TikTok, you know, the Pearson house, this one's iconic. She's such a beauty. That first project, I was actually considering being a partner on it. And I had a couple calls with them. I was really interested. In the end, I ended up declining for a couple reasons.
4:33For one, we're planning to build onto our house and do our own kind of addition and build an ADU. So I just wanted funds for our own property and what we're working on rather than invest it in something else. But the second reason, transparently, was that this was their first project raising investor capital on. And that did make me nervous. Like as much as I love Maddie and Skyler and trusted them in the vision, I was like, I don't know if I want to be the guinea pig on this deal. And so I think that that was like not the main reason, but subconsciously that was that was there.
5:07Natalie Palmer:And I remember, I wonder if I can find the screenshot of this, but I remember when I told Maddie that I was going to pass on it and decline, I literally said word for word, and I know I'm going to regret this because I knew the project was going to just be that successful. Like I knew it and I just let my own stupid fears get in the way. But yeah, I literally texted her saying, I know that I'm going to regret this and spoiler alert, about two years have passed and I do regret it. That property is absolutely crushing it it's doing so well. They've already made returns to partners. That property has been an incredible success.
5:43Since then, they've ended up doing five more after that one. And I've just been watching their portfolio grow from the sidelines for the last two years and have been kicking myself for not being a part of that first deal, but have been watching everything else they're doing and really, really just admired the whole formula that they came up with to make these properties in upstate New York, absolutely kick ass. So meanwhile, while I've just been watching that, I, for the last two years, have really wanted myself to start getting into raising investor capital. And how this happened was, naturally, I've never even talked about this, but I think because of the podcast, because of my network I've built, I have had so many people reach out to me and say, hey, Natalie, I started listening to your podcast because I wanted to invest in short-term rentals.
6:35I'm a high W-2 earner. I wanted to invest in STRs, so I started listening to No Vacancy.
6:40Natalie Palmer:After listening to five episodes, I've realized this is way more work than I want to do, and I actually don't want to invest in short-term rentals, or I don't want to operate and manage them. But I fully believe in them, and I would love to invest. So if you ever have an opportunity or something you're raising money for, let me know. I would love to work with you. So I realized that I had kind of gained a lot of trust with my audience and had a growing number of people who were willing to give me money, which was insane to think about. On the flip side, I've interviewed so many guests. You guys have heard from so many cool people working on really amazing projects on the show.
7:17And at the end, whenever we're done recording, I always chat to the guest a little bit. And so many times I've asked the person like, what's next for you? And so many of my guests have said, well, I have this vision of this amazing property or compound or project or something I want to work on, but I would need X amount of dollars to make it happen. And I don't know where to find that capital. So I've just been noodling on this for like the last two years and thinking to myself, you know, I think that this is something I could do, like be kind of a matchmaker here. And I'm getting interest from the partner side.
7:49I'm getting interest from people who need capital. I think there's something there and that I could be pairing these people up. But I just let imposter syndrome and all these doubts get into my head and, you know, just kept telling myself, who am I to raise investor capital? I don't know what I'm doing. Like, I don't know the first thing about this. So I talked myself out of it for two years.
8:09Natalie Palmer:Finally, this year, Maddie and Skylar are at Level Up Your Listing. And it was the very tail end of the conference. I think actually the whole conference had ended and they were helping tear down their booth and pack away some of the books that they had brought. They were sponsors for STR book club. So we were hanging out at their booth and I just start talking to them. And Maddie ends up telling me that who they had raising capital for them is no longer working with them. And Maddie was telling me, oh, I'm absolutely dreading the idea of having to go back to raising capital. I just realized how much I love sourcing the deals, doing project management, designing the property, and then operating it.
8:47I don't want to be doing all these sales calls and talking to investors. It's so much work. It's a full-time job in itself.
8:53Natalie Palmer:And instantly I was like, okay, wait, this is my, this is my chance. Like I need to tell her what I've been wanting to do. And so I told her, hold on, I think that I can do this for you. I've never raised capital before transparently. Like, you know, this would be my first time doing this for you guys, but I think I would do a really good job. and this is something I've wanted to do for two years now. And so we had another follow-up meeting the week after Level Up, got home, decompressed, chatted. And Maddie said, okay, as soon as we are under contract on a property, we're going to underwrite the whole deal and everything, let you know the terms and what we want with our partners.
9:31But we're going to have you take the lead on this and raise the investor capital. So it ended up being, I want to say like four weeks later, she texts me end of April and she's like, all right, we're under contract. We put in an offer on a deal. It was accepted. Here's everything. These are the returns we can give investors. This is the structure. Here's the operating agreement. I mean, we had a few meetings to get me up to speed on how they structured things. And then I was off to the races from there.
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10:29I think that that offer was accepted or the property went under contract April 20th, I want to say. It was like end of April. And it took me probably about a week and a half to like get the pitch deck together, fully educate myself on the deal, practice my pitch so many times,
10:48Natalie Palmer:kept rehearsing it. Like it took me about a week and a half to get my bearings on this. And then I want to say it was May 1st, I officially started pitching people. And our very last investor we secured on July 30th. So pretty much three months, just under three months, shy of a day, it took to secure the capital for this whole project. And I'm going to answer some questions right now that I know a lot of you are probably asking. These are questions that I had when I started working with Maddie and Skyler on this deal. Again, I had never raised capital for anything. So they had already done six deals before I came on.
11:24So thank God that they educated me through a lot of this so that I knew what to do. But I'm going to answer some questions for you guys that I think that you are probably wondering. So to start off, one thing that I was very unsure of on how this whole thing would work would be timeline-wise, do we secure the investors first and then find a property and put an offer on it, or is it the other way around? And in our case, we did it the other way around. I am sure that there are people who have raised capital the opposite way and they secure all their investors first and then go out and find the deal From my perspective.
12:02I know i've only done one but from my perspective. I imagine that that would be much harder to do Even though it was a little bit scary because we're under contract and we had a deadline And we actually did miss the deadline and had to extend escrow and I will get into that and tell you guys how we handled that But even though there was a lot of pressure from that sense that there was a hard deadline, it did make it so much easier because the way that we wanted this deal to work is that I never consider these people just investors. I never want to consider these people just like, oh, they're just giving us the cash and that's it.
12:39They wash their hands of the whole deal and we'll just pay them back and that's the end of it. we truly consider these people to be partners. They can be passive partners if they want.
12:49Natalie Palmer:They can be silent partners. They do not have to get involved. We want to make this investment as easy as possible. But I think across the partners that we got, they all are so educated. They all have real estate experience. Every partner that we got asked such good questions and was so thoughtful about the investment. And they have ideas on how to make the property even better. And that's what we wanted. I think we wanted a very collaborative group that all saw the vision for the property and saw what we wanted to do and saw the potential. And I think that that was really important. We had to have the property first so that we could put together mood boards of what it was going to look like.
13:28That's how we were able to underwrite the whole deal because we had to know what offer was accepted. If we had started with raising the capital first and were projecting certain returns, well, then what if we were putting offers in, but they got rejected, or we had to go over asking, or all of a sudden we had to buy the property in cash, and we couldn't do a DSCR loan like we did. So many variables would change, and it would basically change the entire pro forma on our end. So I think that for us to really accurately project what these returns were going to be, and have these investors be in the know of how the whole structure worked, what we were going for, what kind of income we were able to make.
14:10We're also going to host events at this property and host weddings. We had to have the right property and know the regulations of that property and what parking would be like and if the neighbors are going to have an issue and if there's a noise ordinance. There's just too many variables, in my opinion, to secure funds first and then go out and find the property. That's just my opinion. But if anybody has raised investor capital that way and gotten the money first and then found out and found the deal, I would love to hear from you on how that works. Like I said, there was some pressure doing it in the order that we did, but I think that it just made it, in my opinion, it was essential that we did it this way.
14:47We had to be under contract, then get all our numbers together and ducks in a row and then go find the partners that fit that property and wanted what we could give them from this deal, from this opportunity. So hopefully that answers that question for you guys, because I know I was definitely wondering that at the beginning. Like, do I have to go out and find these investors first and then we find the deal or how does that work? Now, next question, as far as timeline,
15:13Natalie Palmer:like I mentioned, there was some pressure that we had a timeline and we had to have a certain amount of money raised by a certain deadline in order to apply for the loan. We did not buy the property in cash. We did get a DSCR loan for this. And so to do that, the bank had to see, they told us the amount, but they wanted to see enough for the down payment closing costs. And I think it was three months of reserves that they wanted. And we needed that by a certain deadline. So there was kind of an initial fundraise we had to do. And then once that deadline passed, We applied for the loan. At this point, we're officially in the loan application process.
15:52This is when all the due diligence is done. They're checking financials, everything like that. And in the meantime, I was set out to raise the remainder of the funds that we needed. And this is everything that was going to be used for repairs, renovations, furniture, building out our wellness center, just all of the upgrades that we were going to do to the property. So I kind of had like two deadlines with fundraising to balance.
16:18Natalie Palmer:Looking back, the first deadline was actually less money. I think of the entire deal, let me do the math actually really quick on this. Divide it by. Okay, so for the first deadline, I needed about 37 % of the total amount that we needed a fundraise secured. The rest, so the remaining two-thirds of the entire budget, all came after that first deadline once we were already in the loan application process. So you would think that I'd be more nervous about the second portion because that was just more money, almost twice as much. But looking back, that first deadline had me way more stressed than the second.
17:03Natalie Palmer:And this is definitely something I ran into. I'll get into a little bit of investor psychology because this was just a very curious learning experiment for me. But that first deadline that we came across, it was so I had basically four partners that were really, really interested in working on this deal. And what I heard from every single one of them, this is before I had a single one signed on. What I heard from every single one of them was how many other partners do you have so far? How many other partners do you have so far? That's what everybody wanted to know. And of course, I'm not going to lie.
17:37Natalie Palmer:So I was like, damn, I don't want to tell these people like no one signed on yet. Like that doesn't give them any confidence. But I just was transparent. And I said, you know, we're actively talking to three others, but nobody has officially signed on for this yet. And I think that that made the four initial people that were going to cover that first deadline that we needed. Again, This was closing cost down payment and three months of reserves that the bank wanted to see. Those four people, I think it made them a little bit nervous of just, do I really want to be the first one? If no one else sees the potential in this deal, am I ready to take a chance on it?
18:15But finally, I had one call. One girl officially said, okay, yes, we're doing it. We're moving
18:20Natalie Palmer:forward. And I immediately fire off to tell the other three, hey, we just secured this one. Here's now the new remaining amount. The next three people, those other three people that were already interested and were just skeptical because no one had signed on, they all committed within like the next 48 hours. Like it was just dominoes falling into place. So that was definitely something I learned is that first deadline, getting the first person. And maybe this is just because it was the first deal I ever funded. Hopefully on the next deal, you know, I can say, oh, for this project, we don't have anyone, but I've already funded a deal and I'm sure that that will give more confidence to potential partners.
19:00But for this time, at least, I definitely saw that it was like people needed the confidence that somebody else saw the same potential in the deal. The moment that happened, boom, boom, boom, boom, people were falling into place. So as soon as we had that amount secured, those people signed, they wired in their funds, and then we applied for the loan. So for the next 30 or so days while the loan application was happening, I had set out to raise that remaining two thirds that we needed for the whole project. And this part at this point, even though it was more money, I felt like I was coasting. I mean, I just had so much being able to tell partners like we are already under contract.
19:45We've already applied for the loan, we have a closing date, made the deal feel so much more real. And I will not deny, I definitely think that there was probably like my, what am I trying to say? I think the way that I came off having calls with potential partners after that point, probably completely changed. Like, I don't know that for sure. I should have been recording my calls and gone back and looked at the first one versus the last one I did. But I know something internally changed. I had a completely brand new confidence going into sort of this second round of fundraising. And I really just felt like, okay, yeah, I got the first deadline done.
20:28You know, with having zero experience, not knowing what I was doing, I was able to get that this part will be easy. And the other thing is that with the second deadline, it was a lot more flexible. You guys know that the bank, that deadline was like a very formal thing. Like there was a certain amount we needed. It had to be in the bank. It had to be there by a certain time. If not, we had to file an extension, which again, I will get to because we did have to do that. But that was just so much more pressure. That one felt so much more like legalistic and like real. The second deadline was really just what our team had come up with that we needed for the renovations and to get the property to the standard we want it.
21:09the bank did not care about this amount. This was just truly how much we believed we needed. And as you can imagine, renovations come in phases as well. So I also felt a lot less pressure to have that full amount in the bank by a certain point. Obviously, we don't want this to drag out forever. But I knew like, hey, if we get 100 ,000 wired and future partners aren't biting on the rest, we can go a little bit longer before those funds are moved in because, you know, there's still so much that we can start with with$100 ,000 and then we can secure the rest and get all of this thing buttoned up.
Read the full transcript
21:48We're estimating about four months to renovate this property anyway. So I knew that not all of that money is going to get deployed day one of when we get the keys and start working on the property. Like I just did feel more breathing room to close the rest.
22:05Natalie Palmer:Although my goal was to have it all by August 1st, which, like I said, we got our last investor on July 30th. So we did make that deadline in the end. But yeah, I just personally felt like once I got over the first hurdle, the second one, I was like, now I can show people that we already have investors, we're already under contract, and I walked into it with this whole new confidence. So I was not worried about that second round of fundraising at all. That one, I thought, went so smoothly. And yeah, it was just, I don't know, I got into like a rhythm with this and it was so much fun. Now, let me tell you guys one of the big mistakes that I made starting with this deal.
22:44When we first started with this deal, we had this idea that we didn't want more than four partners. We thought having too many partners is just too many votes and it gets a little bit too complicated. So we went into this deal thinking that we only wanted four partners. So the total investment amount that we had, we divided it by four, ended up being a six-figure amount. And we said, this is the minimum to invest in this deal. And it was crickets. I could not get responses for probably two or three weeks. I think people saw a six-figure number and just, I think it immediately scared a lot of people off that that's just a huge amount to commit to and wire, especially with this being my first time, I didn't really have a network built up.
23:31Again, I had put feelers out there of potential investors, but this was really the first time that I actively said, like, I'm working on this and I'm raising capital for a deal. And then I think to just show up and ask for a six-figure number from people was quite shocking. So after
23:47Natalie Palmer:about three or so weeks of just crickets on this, came back to Maddie and Skylar and we had the conversation to lower the investment amount to 50k. And this made a huge difference. As soon as I had lowered to 50, I re emailed all those people and just said, Hey, update, we were able to lower the investment amount to 50 ,000. The response rate shot up like crazy. And I will say for anyone out there who wants to raise capital and is like taking notes listening to this from my experience, I don't necessarily think that you can't go in with a six-figure number for your deal. Whatever you're raising money for, maybe you want your minimum to be$500 ,000.
24:27I have no idea. I will say don't get scared and think that you have to go with a$50 ,000 minimum because that's what I did. Maybe you need to go even lower. Maybe$15 ,000 needs to be your minimum. I think what I found was that was just my network. The people that I had accumulated, or at least in this phase of my capital raising journey, it seems that the people that I had accumulated, the interest that I had garnered across that audience, 50K was a much more approachable number. Again, this could be completely different for you. If you are a surgeon, a doctor, a lawyer, and you have a great income and your entire audience and close network are high, high W-2 earners and very wealthy people, and if you are raising capital for a deal, I have no idea.
25:20I mean, maybe for you,$250 ,000 is a very reasonable minimum to ask from your audience. I really noticed that six figures was pushing what I could get from people. So we ended up switching it to a 50k minimum. And again, immediately response rates started coming through. I had re-emailed everybody that we were able to change and interest was coming in fast. So 50k was a number that really worked well for us. And I'm so happy that we did that because in the end, we had a couple partners that once we got them on the call, they were actually interested in investing as high as$100 ,000. So I noticed that that$50 ,000 was just more of a foot in the door, like, okay, I'm able to just get them on the phone and have this conversation and present the deal to them.
26:05And then they might be interested in doing more than$50 ,000. But I think that just that initial email reach out, that it was a six-figure minimum, that scared people off. I think our exact minimum to start was like$120 ,000. and yeah I guess that that just was not approachable at the time so lowered it to 50 and everything changed from there unfortunately because of that we basically lost about a month in the timeline like I said it took me about a week to 10 days to even get my bearing straight for the first initial pitches and then it was probably three weeks of just silence and not really getting responses so luckily when Maddie had put an offer on the property she had specifically submitted the offer and said she wanted a 60-day escrow.
26:52Natalie Palmer:So we did have some time on our hands, but basically the first month was just gone from kind of like us figuring out the right amount and how to target these people. So once we changed it to 50, everything in the deal changed, responses started coming in, and it really felt like it was falling into place. And from that point, by the time that we did secure that first amount, that first deadline of closing cost down payment and the reserves. By the time we did that, we had actually passed our deadline for when we were supposed to apply for the loan buy. And I know that the seller was not happy about this.
27:29Natalie Palmer:And I want to tell you guys what we did to make this right. So this is your warning that, hey, things, if you are out there raising capital, things will go wrong. We absolutely made mistakes. Although I'm very happy to say that Maddie told me that she felt like this was one of the smoothest closes that they've ever did. So if that was my first time, I figured some things out. Like we did make it as smooth as possible. But absolutely, like I missed that first deadline. And that that is on me. I think I should have we should have lowered the amount sooner and just been more aggressive following up with people.
28:04But I want to tell you guys, if this happens to you, it is not the end of the world. If you miss that first deadline, here's what we did to make it all right. So the seller, of course, was not happy. I guess that she had already bought a new property and she was counting on the funds coming in. Of course, she was now paying the mortgage still on this property as well as on the new one that she purchased. So she was paying two mortgages and she was not happy that we asked for another 30 days. Her agent had come to Maddie and said, hey, would you guys maybe be willing to split this month's mortgage 50-50 just to help make it a little bit easier on the seller because she's pretty upset.
28:46And we ended up deciding, I think that she wanted, I think that her mortgage was like$3 ,000 a month. So she wanted us to put in like$1 ,500. I think that we ended up coming back saying, we will cover$3 ,500 for you. So even more than her$3 ,000 mortgage. But we just really wanted to make it right. So we felt so bad about taking the extra month and taking longer. And once we offered that and paid her even more than that mortgage was worth, instantly the seller was
29:14Natalie Palmer:happy and pacified. So just letting you guys know, don't, I mean, like I said, I should have been doing this for two years. Like this is what I've had interest in doing for two years. And I talk myself out of it so many times because I ran through these scenarios of what if this goes wrong? What if this goes wrong? Guess what? It did. Stuff did go wrong and we did miss deadlines and we did have to make it right. But you figure it out and you make it right. So for anyone listening to this that is wanting to jump into capital raising or wants to raise money for a deal, I promise you things will go wrong that you can't prepare for.
29:49You'll figure it out. So that's definitely one mistake we made, but I'm really happy that we made it right and that seller was content in the end. We went above and beyond for her just to make sure that she did not
29:58Natalie Palmer:have to carry two mortgage payments at the same time. While we're on this note, I'm going to get into something else that I did wrong. Another mistake that I made with capital raising. I hope you guys are enjoying this episode. I'm like really laying it all out there. Okay, here's the next thing that I did wrong. My initial email, the pitch that I had put together to investors, I truly approach this initial pitch like all wrong. And the next man, the next deal I do is going to be so much better and smoother. I will not make this mistake again. So here's what I think I did wrong. My very first pitch that I had sent to investors, it was short and sweet, which I think that was good.
30:41You know what? Let me pull it up. I'm just going to actually read it to you guys so that you know exactly what I sent and so that you don't send this. Oh, and before I read the email, let me tell you guys how I got these contacts. I had put together a quick Google form that was asking, you know what, I'll link it here. And you guys can, hey, if you're interested in working on the next deal, you can fill it out yourself and I'll have your contact info. But if you just want to
31:02Natalie Palmer:look at the form to see what questions I put, this form was extremely, extremely helpful. So I will link that here. And hey, I won't be mad if you fill it out and want to be a potential investor on the next deal. But anyway, I'll link that here. And so that's how I found almost everybody that I had reached out to was they had come in through this form and that's where I got their email to start pitching them. So once I had that, this was then the email I sent. Hi, Blank. Thank you so much for expressing interest at the newest For the Love of Upstate project. I'm excited to now be working with FTLOU to help secure capital and identify ideal partners.
31:38I'd love to see if this deal aligns with your investing goals. Quick links. I linked our pitch deck, which I had made in Canva. Then I linked the Zillow link and the Proforma. And then I wrote deal overview, bullet point with three bullets. Our target capital raise is X amount with this deadline. I said our minimum investment is$50 ,000 and the projected returns are 14.66 % plus equity split. If you'd like to explore further, you can book some time with me here, linked my Calendly or feel free to call or text me directly and put my cell number.
32:15Natalie Palmer:That was it. And I actually think that this email structure was fantastic. The mistake, I in the future will not be linking the pro forma. So two mistakes here. I should not have included the pro forma. And what I should have included instead is a loom video of me explaining the pro forma. So even at this point, when we had changed to the 50k minimum, and I re engaged everybody that the minimum was lower. Like I said, response rate did shoot up, but I still out of everyone I had emailed, the response rate was not what I wanted it to be. Finally, after having a few calls, I realized the questions that I was getting over and over on the pro forma.
32:59So I sat down and I recorded like a 30 minute loom video of me breaking down the whole deal and going through the whole spreadsheet with the investor. And then the people who still had it replied, I went and emailed all of them linking that loom video. And I said, Hey, I recorded this video breaking down the deal in further detail. Hopefully this is helpful to make sense of the Proforma sent that out. That video, I think single-handedly closed us like five of the eight investors. More than half the partners came through once I had put that Loom video together. It was an absolute game changer to have something that really explained the deal.
33:45And I also think it put a face behind the deal. I mean, everyone I had reached out to either came from my podcast or my Instagram or my email. So they knew who I was already. But I think there's just something so different about you sitting there and walking them through the whole process and putting it in a video where they could watch the deal on their own time. They could rewind if there was parts they didn't understand or they needed to see a breakdown over and over. They could slow it down. They could speed it up. It was so I mean, like I'm telling you guys, I will never again ask for capital without recording a video first.
34:23And I wish that I hadn't even included the pro forma because I noticed this is so sad, but I actually had about three people who were interested in the deal. And once I got them on the phone and we were talking through or we got them on Zoom, I actually had three people who ended up passing on the deal because literally because what they told me was, I'm really interested in investing in something like this. Like I love Maddie's design. I trust your guys' team. I know that you guys will do good with the money that I invest. But I want to understand every single part of what I'm investing in. And this pro forma, I find it really overwhelming.
35:05And because I don't understand it, I just don't want to move forward, which is a completely, completely respectable position. I totally get that. You want to know exactly where your money's going. And if you don't 100 % understand something, it's very hard to suddenly wire$50 ,000. I totally get it. And so in the future, I will not be including the pro forma in my pitch deck, in my initial pitch email. And I want to be very clear, it's not because there's anything to hide or that there's like a lack of transparency. If anybody specifically asks for or requests the pro forma, I will email it to them instantly.
35:43And in our pitch deck, I will include screenshots of the pro forma, like certain parts that I think is important for them to know. But honestly, it is a very overwhelming spreadsheet. And even if you've invested in real estate before, if you're somebody who's invested based on just a gut feeling or you know the market or you walk into the house and you just have a vision and you know that you can make it something special, if that's the type of investor you've been and you've never put together a spreadsheet like this, it is very overwhelming and robust to understand. And I think it scared a lot of people off, which is just such a bummer because it was meant to have the exact opposite intention.
36:21We wanted to give all the information up front. And what I liken it to is if you're going to the car dealership, you know, all of us have bought a car before. When I go buy a car, I care about,
36:35Natalie Palmer:this sounds so superficial, but like I care about the color of the exterior, the color of the interior, how many cup holders it has? Is it going to get me from point A to point B? Like, that's what I care about. And I'm already trusting. I don't need to go and open the hood of the car. I wouldn't even know what I'm looking at. Car nerds out there right now are going to judge me for this. But if I go to a car dealership, I will not even ask the car, the salesperson, can you open the hood of the trunk for me so I can take a look at this? Because I would not even know what I'm looking at. And I think that that's what I did.
37:10I think that mistakenly, I gave people what's under the hood of the car, when most of the investors already took for granted or assumed, oh, this investment is going to get me 14.6 % returns. I just want to see, do I like the house? Do I like the color? Do I like the mood board? Do I like the location? Do I feel good about it? Do I feel that this is something I want to be an owner in. So that was a huge learning lesson to me was that in my quest to really inform and educate the investor, I actually think I ended up undermining the deal with a few partners. On the flip side, I did have a couple people say, I need way more information than this.
37:52Can I review the operating agreement before we move forward? Can I see past historical data of other projects that Maddie and Skyler have launched. There were people who asked for way more information than I provided, and all of that I was so happy to give them.
38:08Natalie Palmer:I also ended up recording Loom videos for those before I sent them because I had learned how valuable it was to do the video breakdown. But for people who want more information, right, the person who does know cars and wants to see under the hood, if the car salesman said, no, you're not allowed to look under there, that would immediately set off alarm bells. So I think it's completely fine to be transparent and show the investor more if they want it. But boy, oh boy, did I learn like just giving people all this extra information to digest on their own was totally the wrong approach. So moving forward, I think that that email I sent was fine.
38:48But instead of the quick links that I share being the pitch deck, the Zillow link and the pro forma. I will only include the pitch deck, Zillow link and a link to the loom video. And inside our pitch deck, I will not put the entire pro forma. I'm only going to put screenshots of the critical parts.
39:09Natalie Palmer:Again, if any of you want to invest in the future and you are that person that wants the whole pro forma and wants to see everything, email and let me know. I am more than happy to send all of that info to you. upon request. But yeah, I really learned that like that did not need to be in the initial email. So that was a huge thing that I will be changing for next time that I'm pitching people. Okay, next up, let's pivot to what is everything that I slash we did right? Because there's a lot I have to pat ourselves on the back for and give us credit for here. In the end, we did raise it. So and we were right under three months.
39:46Natalie Palmer:So we we did a good job. We crushed it. And I'm very proud of us. So I want to give credit for the things that we did that worked really well. First was our repayment terms for this. The terms of the deal for partners were so generous and so competitive. And I am really, really proud of this. And I have to give credit to Maddie and Skylar for this, because when I initially started working with them and they told me, hey, this is how we underwrote the deal. We want to give investors 100 % of profits until they are paid back. And then we'll change the structure to 50-50. They all get equity in the deal.
40:25When they walked me through what investors get out of this, I literally told them, I said, I think that this is too much.
40:33Natalie Palmer:I think that you can scale this back. 14.66 % return, 14.66 % is a high return rate. And that was based off our median projection. So I actually think we're going to surpass it. That is a high return rate, you guys. Most people out there raising capital, and I had consulted with a lot of friends and industry peers who have raised capital. Almost everyone that I talked to said they used to do 10 % to 12 % returns. And in the last couple of years, they've changed it to 8 % to 10%. That that's pretty much what the industry standard is. And what I also learned is a lot of times when they're giving you somewhere between that 8 to 10 or 10 to 12, equity is not included.
41:15You're just getting your money back with interest and that's it. So the fact that Maddie and Skyler wanted to give investors 14.66 % returns and equity in the deal, and there's no point where the investors are repaid and bought out of the deal, even once they earn their initial investment back, they stay on and they're continuously making cash flow. And then, of course, they retained that equity. These terms were so generous. And I had told Maddie and Skyler, I don't think we need to put this much in here. Like, we are still very competitive with other people raising capital and other real estate opportunities without all that.
41:53And they, to their credit, said, no, like, we want these to be the terms. We really want our partners to make their money back as quickly as possible. We want to give them 100 % of profits until they're paid back. We want to keep them on. We want them to have equity. They had the vision of how generous they wanted the terms to be to investors. And funny enough, if anyone here is in STR book club, Maddie and Skyler's book club they started, during the time of raising capital here, we read The Purple Cow by Seth Godin. and reading that book it is all about how you have to do something radical to stand out today and there are a lot of people trying to raise capital for real estate deals we are not the first by any means i am absolutely not the first person to come around and try to get people to trust us with their money reading that book completely reassured me that we were on the right path with this.
42:55That yes, maybe these terms were generous, but in today's market with how competitive it is and how many people are asking their wealthy high net worth friends for capital, we have to do something above and beyond. So if any of you read The Purple Cow while we were in STR Book Club, you'll know how much Seth Godin had harped on this. And that was just hitting me the whole time I read that book smack in the middle of this capital raise. And it just really reinforced to me that like we were onto something like these terms being so generous is what was going to set us apart so many of the partners that we signed on already said i am telling my friends about this for the future for the next deal um even people that said hey i'm not financially ready right now i love these terms and i want to work with you guys please keep me posted for the next deal i think that these investors that we did sign on are going to earn their money back with us so much faster than they would with another deal that, you know, the hope is they'll just continue reinvesting into future projects we do.
43:59So I absolutely believe that that was the right formula.
44:03Natalie Palmer:So very, very props to Maddie and Skylar on that one, because I had told them, I think the terms were too generous and they insisted. So I think even Maddie had said, when I told her, I don't think that you need to provide all of this. Like, this is a lot. I think she even said, she was like, you know, my CPA said the exact same thing that we do not have to give investors this much, but I want to. So bravo, round of applause, props to her for knowing what these investors wanted. So that's one thing that we definitely did right was just the deal structure being so competitive and generous. The next thing that I did right here, and this was a hard one, but the next thing I did right and have to give myself credit for was pushing away investors that were not the right fit.
44:45And this was hard to do, but there were actually three people that I intentionally said, we had conversations. And I think if I really put my sales hat on, I could have pushed these people over the edge. I could have gotten them to. But it was a tough call. But I realized I just don't think that this structure is the right fit for these people. And there were three people that after going back and forth, I said, maybe this isn't the right fit. And I can keep you in mind for future opportunities, or we can try to do a different type of deal with you, or work with you one on one rather than doing a partnership.
45:22There was three people like that, that I had to have that conversation with.
45:25Natalie Palmer:And at the time, I was like, what am I doing? I don't even have all these funds secured. We have these deadlines we have to meet. Like, if someone's interested, we should take it. But I just had to trust my gut that in the long run, I didn't want to mislead anybody. So I'll give you guys an example here, so it's not so vague. But we had one partner, for example, or one potential investor, who specifically said, I want to make all my money back within 12 months. And she said that they were starting a new construction project in a year, and she didn't want money tied up for the way that this deal was structured was that money was going to be tied up for seven years, You'd start earning it back within year one, but the full repayment would happen by year six.
46:08And then you get the big equity payout in year seven when we sell. And she didn't want to wait that long. And part of me was thinking like, maybe just for one partner, we could do more of a hard money structure with her and pay her back with interest, you know, within one year. And she won't get any equity in the deal. So it's not going to dilute equity for the other partners. I was running through these scenarios of how do we make this work? I didn't want to take no for an answer. I wanted to see how can we pivot. And in the end, I just realized out of respect for the other partners who had signed on and had agreed to this structure, it wasn't fair to bring somebody else in who didn't see the vision and why we were doing the seven-year hold and what was the point of this.
46:56And again, nothing against this investor. They had their own goals. They had to have their money back within 12 months for a different project. Totally respect that. And maybe a future deal we do, we can do more of hard money terms and just pay you back within a year with interest. Like maybe we could find an opportunity like that. But for this deal, that wasn't how it was structured. And so we kind of had to say, you know what, let's just not force this. Like it seems like it's not what you guys want. It's not really what we want. But I will keep you in mind for the next deal if we have something that works more like this.
47:28Natalie Palmer:And it was super cordial. You know, we respectfully like parted ways like no bad blood there. I still have a great relationship with all three of those people. And I'm sure we'll find a way to work together in the future. But at the time, I was like, Oh, that sucks. Like having people that were like wanting to work with us and just not being able to be flexible on the terms like did I do the wrong thing. and I'm so happy that I trusted that because in the end I think I still had three partners to go when I had said no to some of those people those next partners that came I'm not even kidding you guys but I specifically had the next partners asking questions like what type of partner are you looking for for this like who is this a good fit for and I was able to just clearly define who it's a good fit for because I had just turned people away who it wasn't a good fit for.
48:20Natalie Palmer:So I was so prepared with that answer. And when what I said checked the exact boxes of what these partners were looking for, these were people who had no problem with their funds being tied up for seven years because they're high income earners or whatever, or that this was supposed to be going to an account that they weren't even going to touch for several years. Like, it was just so smooth the way that everything fell into place and being able I actually told them we've turned people away who were not the right fit and I think that being able to say that helped give so much confidence in the deal like I'm not just selling you on this trust me I've already turned people away like I'm I'm pitching you on this because I know that this fits your needs I know that this is what you want as an investor and this aligns with your goals you can trust that I'm not just selling you a pot of bullshit because I've already turned people away.
49:14Just being able to do that, I think, instills so much confidence. So that is one thing that I did right this time and plan to continue every time. I never want to get to a point where I am bending and manipulating the terms just to make it fit when it's just not a right fit. Like this whole, this capital raise really proved to me, in the end, we needed eight partners. There are eight people out there who are going to want the terms that you came up with. If they are fair and you've got an operating agreement to back it, you can find eight people that will want what you've created. So that was just a huge confidence booster that we don't have to like fit something that's just not going to work.
49:55Natalie Palmer:Ultimately, the biggest lesson I learned from this whole thing is that this is all about relationships. Raising capital over and over and over what I heard from the partners we secured, even potential partners who maybe didn't sign for this one, but said, keep me in mind for a future project over and over. What we heard was, you know, this is so different from anything I've done. I've never invested in anything like this, but Natalie, I trust you. And I followed Maddie and Skylar forever. And I trust them. I think every single partner who signed told us some form of that sentence. And that really showed to me, you know, even though I do think our repayment terms were extremely generous and we were prepared and I think our pitch deck kicked ass.
50:43Natalie Palmer:I think the deal kicks ass like so many good things were working in our favor. But at the end of the day, this was just a people business like these partners had to just know, like and trust us. And that's what gave them the official confidence to sign and wire funds because it's a big decision. So that do not Underestimate anyone out there that wants to raise capital, how important it is to just pitch people that you have a good relationship and just always be fostering relationships. Really listen to people in what their goals are. If it's not the right fit, do not force it. There will be another opportunity to get funds from them in the future.
51:20Natalie Palmer:And just always go back to that. These partners, yes, they're signing on to a deal, but they are signing on with you. they have to trust you before they even care about the numbers on the spreadsheet that's my opinion all of this I'm saying after having funded one deal you guys so again I am not the expert but this is a three-month journey and man I learned a lot there's a lot I'll be doing differently next time but a lot I will continue to do the same that I think worked really well overall the biggest thing I have to say though is that like I found my I don't know my calling I think my calling is to be a mom but career-wise this was so much fun for me and so rewarding and it's just so cool to have found something that I'm good at and enjoy and I almost took that for granted to me this whole capital raising thing came so naturally and so effortless like I got on calls with these people And even at the beginning when I was nervous, I just really enjoyed it.
52:26And I just loved having
52:27Natalie Palmer:these conversations and getting to know these partners and having these relationships. It was so much fun for me and so rewarding. And yeah, like I said, I almost took it for granted. But there was a certain point where I talked to a few people about what I was working on. And, you know, kind of went through, yeah, this is what I'm focused on. I'm doing investor relations and I'm working with Maddie and Skylar. Maddie's finding the whole deal and she's designing it. And then Skylar's overseeing the launch and renovations and watching over the construction crew. And then Vance, our COO, he's handling operations and more of the management side of things and putting on all the systems in place.
53:08Natalie Palmer:And I was really breaking this all down. And I talked to a few people who said, like, what did they say? They specifically said something like, oh, you got the short end of the stick to me. And they were like, I would hate having to talk to investors all day or like be on call or basically be doing sales. I would hate that. And they were like, oh, like what Maddie's working on sounds like the dream. I'd love to live in these properties and renovate them. And I was just floored because I have so loved what I've been doing. And to me, I'm like, damn, Maddie, like, how are you ready to go to these projects back to back to back and live on site and endlessly be picking wallpaper and doing all this and doing the grunt work.
53:50Natalie Palmer:Like, how do you do that? That to me is so impressive. But I had people say the exact opposite to me. And it just really reinforced another STR Book Club book that we read recently, but Buy Back Your Time by Dan Martell. I feel like the last three months, I mean, And I worked like I hustled for this for sure, like multiple calls, multiple follow ups, a lot of strategy going into this. I definitely worked to raise this capital like it did not come with zero effort, but it felt effortless because it's just it felt like I was using my gifts and getting to talk to people and tapping into this network.
54:28Natalie Palmer:I've built over the years of having no vacancy and having level up your listing and the community that I've built. It just felt effortless, even though I look back and I'm like, wow, I really worked hard on that, but it didn't feel like work. And I'm sure that Maddie feels the same way. I know she's busting her butt on these deals, her and Skylar both, and our COO, Vance, he's got so much work to do on the operations front, but it feels like everybody found their genius zone and where their groove is. I'm just so grateful I get to do this and so thankful to Maddie and Skylar for giving me a chance to raise capital for this first deal.
55:07Natalie Palmer:I cannot wait for us to get started on the next one. They're already submitting offerings out there. So we'll have a new one very soon if you're interested. And I'm like itching to start raising for the next one and apply everything I've learned. Yeah, it's just been truly so fulfilling. I remember the first two investors who signed on for 50k each, I walked around the house the entire day with like the dorkiest smile on my face. And I just like would go up to my husband, Eric. And I was like, I can't believe I got$100 ,000 worth of people to trust me, which is, I mean, pennies like to compare to people who have raised millions and millions and millions of dollars.
55:50Natalie Palmer:Like my first hundred thousand is so minuscule, but you guys, I walked around the house for like a full day and I was just like, I got$100 ,000. I got$100 ,000. Obviously, I didn't get$100 ,000 that's going towards the deal and everything. But the fact that like I instilled that confidence with these people and got them to sign and wire it like that feeling was just, I was on cloud nine. And then the same thing happened the day that we fully funded the remainder of the project. Again, I just walked around the house for 48 hours. And I was like, I can't believe I fully funded it. Like I probably just looked like an idiot walking around smiling in my house.
56:27Natalie Palmer:But it just is so fulfilling. And I have all the confidence in the world. Like this deal was so special. And I cannot wait to have this one launched and start cranking out money and returns for these partners. I'm so excited for like our first quarterly call with them once we're generating returns and just to maintain relationships with these people over seven years. It's going to be such a fun group we're working with. Every partner that we found for this deal is just so aligned on their real estate goals, why they invested in this. Yeah, it's just such a fun group. And I truly walked around the house like an idiot for like multiple days over getting to do this whole thing and play a part in this.
57:16Natalie Palmer:So anyway, thank you guys for hearing my rant. I hope if anybody out there is also interested in raising capital, you took some nuggets of this that was helpful. Like I said, I will link the form that I had made below. Fill it out if you want to be an investor or if you just want to take a peek at it. That form was really helpful for me to just narrow down the goals and the budget of potential investors. And that was really where almost every partner that we secured came through that form. So that was essential for me to have and just share that, make something like that, you guys, and share that with your email list, on your socials, whatever network that you have, throw it on LinkedIn.
57:55That was really helpful for me to start gathering these people. And again, not every one of them was the right fit for this deal, but I just have so many contacts now that I know I can go to for the future.
58:06Natalie Palmer:All right, that's it. That's a wrap for this one. And I will see you guys back here next week. And with that, it is now checkout time. Thanks for listening. And I'll see you back here next week. lastly as airbnb hosts we all can appreciate a good five-star review so you already know a great review on this podcast would mean so much to me please subscribe review share and connect with me in the show notes below bye
58:49We'll be right back.
From the publisher
This week I'm going solo on the mic breaking down every nitty gritty detail of my latest project... drum roll please... raising investor capital for a luxury, waterfront Upstate New York property! As I write this, I'm happy to announce we officially closed and all funds have been wired.
All that to say, I definitely made some mistakes with how I went about this. And today I'm sharing the good, the bad, and the ugly. In this episode I'll take you through the entire process, start to finish, and detail what worked and what definitely did not.
As promised, here's the investor interest form I mentioned in today's episode. Either copy it for your own purposes, or fill it out if you want to partner on a future deal!
Episode 156 with Madi Johnson
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