I Quit My W2 Job After a “Home Run” First Deal (With No Money or Experience)

Summary

Real Estate Rookie — Episode Summary

Episode Title:

I Quit My W2 Job After a “Home Run” First Deal (With No Money or Experience)
Date: November 3, 2025
Hosts: Ashley Kehr, Tony J. Robinson
Guest: Chris Rickenbaugh

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Episode Overview

In this episode, Ashley and Tony sit down with Chris Rickenbaugh, a true “rookie” investor whose story epitomizes diving in headfirst, learning on the job, and demonstrating that action trumps endless preparation. Chris chronicles how he went from zero experience and no money to completing a highly successful first flip, quitting his W2 job, and rapidly scaling his investments—then weathering the hard-earned lessons of growing too quickly, partnership missteps, and what it takes to course correct when things don’t go according to plan.

This candid conversation offers both inspiration and practical takeaways for anyone considering their first (or next) real estate deal—especially those nervous about starting without perfect resources or a robust safety net.

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Key Discussion Points & Insights

1. Chris's First Flip: Confidence, Resourcefulness, and Action

• Finding the Deal

  • Chris found his first flip in 2024 via the MLS as a relatively inexpensive, “cosmetic only” opportunity in his neighborhood.
    "[I] saw this house... priced kind of low. I know this area really good. I know I could sell it at about $225K... Let's put an offer in." (02:00–02:20)

• Raising Capital Creatively

  • Lacking his own funds, Chris relied on hard money lending and an unexpected connection: the owner of an Airbnb he had previously stayed at, who became his first private money lender.
    "You just booked an Airbnb somewhere, forgot something inside... reached out to the person... and they became your first private money lender?" —Tony (02:54–03:18) "Yeah... We got to know each other when I was doing a live-in reno... We stayed in touch." —Chris (03:19–03:43)

• Executing the Flip

  • Chris leveraged a contractor sourced through his lender; renovations were completed in 12 days, and the house went under contract within two days.
    "They knocked the house out in 12 days. So it was a home run." (01:46–02:00)

2. Building Confidence and Taking the Leap

• Learning "Just Enough"—Then Acting

  • Chris's confidence came from consuming podcasts (notably BiggerPockets) and books, but crucially, taking action by creating his own scope of work and networking with contractors and agents—even before he had all the answers. "It was a lot of listening to you guys... then I started to take action." (04:14–05:19)

• Action Over Analysis Paralysis

  • Ashley underscores the importance of implementation versus endless learning, sharing her own procrastination experience.
    "Everyone can listen. But will you actually take action?... Chris, you did exactly that." —Ashley (05:55–06:24)
  • Chris echoes:
    "The action is definitely the thing that sets you apart." (06:24–06:32)

3. Overcoming the Fear of Raising Money and Rejection

• No Experience? Start Anyway

  • Chris had never raised private capital before, but the necessity of funding forced him into outreach and, ultimately, success. "No raising money, no capital, just trying to be a good person, being transparent." —Chris (07:51–08:22)

• Handling Rejection & Persistence

  • Chris reframed rejection as a numbers game:
    "You're going to get a ton of no's, but it only takes one yes." (09:09–09:33)
    "When your back's against the wall, you have to do something." (10:29–10:42)
    "Cold calls—you're going to get 120 no's, but it only takes one yes." (10:40–10:56)

4. Scaling Quickly — The Double-Edged Sword

• Shifting Analysis with Experience

  • After his first flip, Chris realized each project gave him cost and scope benchmarks for the next.
    "So now you have a little bit of data... what did I spend on that kitchen?... You have a little bit of data going into that next deal." (13:57–14:29)

• Quitting the W2: Six-Month Runway

  • Chris left his sales job after his live-in flip. He calculated he needed $4,000–$5,000/month to survive, aiming for at least one $20K profit flip per four months.
    "I got six months to figure it out... about four to $5,000, if I could make that every month I'd be safe." (15:27–16:36)

• Budgeting and Contractor Reliance

  • Chris relied heavily on contractor estimates (often calculated per-square-foot) for rapid renovation budgeting:
    "If we need to do everything on the interior, about $45 a square foot... for a 1,000 sq ft house, that's $45,000." (18:37–19:38)

5. Pitfalls of Rapid Expansion & Bad Partnerships

• Project Delays & Overruns

  • Chris encountered significant delays and budget overruns, particularly around permitting and inspections:
    "For my second deal... it delayed us three months... big learning curve." (19:44–20:11)

• Partnership Issues & “Domino Effect”

  • Chris's partnership with an experienced flipper quickly went south due to poor financial management, wrong ARV estimates, and personal red flags. "None of these flips were selling, none of the houses were even close on the ARV... Oh my gosh, I've made a lot of mistakes here." (25:15–27:36)

  • He realized the importance of careful vetting—sometimes only possible by “trying on” a partnership in a single project:
    "The biggest part was the money... losing hundreds of thousands for people, owing hundreds of thousands, being in a really, really bad position. You become the five people you hang around." (25:15–27:36)

• Scaling Advice from Tony

  • Tony shares his own struggles with “scaling for the sake of scaling”:
    "As a new investor, especially when your first deal goes so incredibly well, it can become almost addicting... Don't scale just for the sake of scaling..." (22:25–24:58)

6. Recovering and Course-Correcting

• Damage Control & System Building

  • Chris enters “damage control” mode: selling off properties, restructuring loans, joining a mentorship community, and creating clear systems before considering further flips. "Now that the pieces have stopped moving, I’ve been able to figure out where I’m at... I’m not going to go buy five projects all at once." (34:45–36:29)

• Building Out Sustainability

  • Chris begins diversifying, converting his first home into a midterm (45-day) rental, and purchasing a new home via subject-to financing.
    "We just turned our, my first house into a medium-term rental... we just bought the house that I'm in, a new primary subject to." (37:22–37:26)

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Memorable Quotes & Timestamps

• “If you have the deal, you're going to be able to find the money... It only takes one yes to be able to raise the money.” —Chris (08:55–09:33)

• “Action is definitely what sets you apart... Once you get in and start taking calls and walking houses, it gets a lot less scary.” —Chris (06:24–06:56)

• “When your back's against the wall, it's like you have to do something... You're going to get a lot of no's, but it's only going to lead you to a yes.” —Chris (10:29–10:42)

• "You're learning so much more through your mistakes than anything that goes right... I wouldn't trade that for the world." —Chris (38:09–38:50)

• "Your network is your net worth. I really learned that through this process." —Chris (39:35–40:08)

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Rapid Fire Rookie Tips (37:22–40:08)

Most Proud Of:

• "Being able to get started. Action puts you ahead of 90% of people who just listen and read." (37:35–38:07)

Biggest Rookie Mistake:

• "So many mistakes, but you learn more from what goes wrong than what goes right." (38:09–38:50)

Advice for First-Time Flippers:

• "Start walking houses and taking action. Call agents, go to meetups, talk to wholesalers. You have to put yourself out there." (38:57–39:27)

How to Model Other Successful Investors:

• "Go to meetups and shadow other investors. Bring them deals, bring them value, and copy everything they do." (39:35–40:08)

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Where to Follow Chris

• Instagram/TikTok: @Chris.Rickenbaugh
• Podcast: Leadway Wealth Builders podcast

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Key Takeaways for Listeners

• Don’t wait for the perfect moment. Start with whatever knowledge, resources, and confidence you have—action builds confidence.
• Raising capital is less about experience and more about relationships, persistence, and transparency.
• Be careful who you partner with; the wrong partner can create financial and emotional chaos.
• Scale deliberately, not reactively. Finish a deal, learn from it, and then move to the next.
• Learn to analyze and budget by leveraging data from your past projects and relying on honest contractor input.
• Mistakes and setbacks are inevitable but are often the richest source of learning. Build better systems and communities to bounce back stronger.

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This episode is a must for any new investor (or aspiring one) looking to turn curiosity into action—and to prepare for both the exhilarating wins and the inevitable bumps on the journey to financial freedom through real estate.

Transcript

[A]

Tony, one of the scariest but most exciting things about real estate is your first flip. And today's guest didn't just survive his first one, he crushed it.

[B]

Yeah, but the real story isn't the flip that went perfect, it's what happened after. Because our guest today, Chris Rickenbaugh, learned more from the mistakes, the setbacks, and the partner issues than he did from the first home run.

[A]

Exactly. And he's only been in the game since 2024, but in that short time, he's bought 10 deals, flipped houses, raised private money, and even dabbled in midterm rentals. Today, we're diving into what he learned the hard way and how rookies can avoid some of these same pitfalls. This is the Real Estate Rookie podcast, and I'm Ashley Kerr.

[B]

And I'm Tony J. Robinson. And with that, let's give a big warm welcome to Chris. Chris, thanks so much for joining us today, brother.

[C]

Absolutely. Thank you guys for having me on. I've been a longtime listener.

[A]

Chris, can you walk us through your very first flip? How did you find it? How did you raise the money, and what did this first deal look like?

[C]

Yeah, that first flip back in 2024, just a little about a year and a half ago, I found it on the ML mls. So I was working on trying to find expired listings, maybe some subject to opportunities. And I just was scrolling Zillow, saw this house that was in my neighborhood, it was priced kind of low. And I said, you know, that house doesn't look bad. It just needs touched up in the middle. So I called the real estate agent I was working with and said, hey, I, you, you like to walk this house, let's see what we can do. So we walked it and I said, okay, well, I know this area really good. I know I could sell it at about 225. And I said, let's put an offer in on it and see where it goes. So we put an offer right at their number. It got accepted a couple deal or a couple days later. And then, you know, we went into the money raising game. So that's the, that's easily the scariest part. So after about a week or two of calling around, I got set up with hard money. We were ready to go. I was, you know, kind of at the end of, end of my contacts, like, oh my gosh, who, who do I reach out to? So I actually texted somebody whose Airbnb I stayed at. We sat down after I forgot my remote in his apartment, and he said, you know, if you have any opportunities come up, just let me know. So I shot him a text and he said, yeah, man, let's. Let's sit down, let's go and walk it. So we walked it, and I had to raise 35,000 to be able to purchase the home. And he says, yeah, man, let's do it. So that's how we ended up purchasing the home. We found a contractor who he knew, and they brought his buddy down from Connecticut who's a general contractor up there. They knocked the house out in 12 days. So it was a home run. And then it was under contract to sell within two days of being on the market.

[A]

Okay, I need to start taking notes because there's like 20 things I want.

[B]

To ask you right now. Ash, I know you got to follow up, but, Chris, I just want to. I want to make sure I understood this correctly. You said that you stayed at someone's Airbnb, someone who you didn't know, you just booked an Airbnb somewhere, forgot something inside of that Airbnb, reached out to the, like, the person who was hosting that unit, and they became your first private money lender. Am I, am I understanding that sequence of events correctly?

[D]

Yeah.

[C]

So how we kind of got to know each other was when I was doing a live in renovation on my personal house because I originally bought it to be a medium term rental. And I said, you know, I had a couple questions about Airbnb. And he said, yeah, man, let's sit down.

[D]

So pretty much, pretty much went from there.

[C]

We're doing the live in renovation. I didn't have a bathroom for 10 days, stayed at his Airbnb, and that's how we got to know each other.

[A]

That's an incredible story. So during the whole time of you telling this story and about this deal is you just screamed confidence. You seemed very confident as to what the ARV was going to be. You seemed very confident that you could get this deal under contract and you.

[E]

Could find the money.

[A]

You didn't have any money lined up. So walk us through. How did you actually become confident in analyzing a deal, knowing what the ARV was, and knowing that you could go out and find funding for this deal?

[C]

Yeah, it was a lot of listening to you guys, truthfully, and lots of bigger pockets. Because at the end of 2022, I was, you know, about to graduate college. I started reading real estate books and then I started listening to the podcasts and pretty much went from there. That's the end of that year, I bought my first house as a fixer. Upper. It was livable, but needed a whole bathroom, needed flooring, needed windows. So I was, you know, listening to your podcast, and, Ashley, you talked about, you know, how you create your scope of work. So that's what I did for this house. I listed everything I need done to it room by room, and then was able to hand that to a contractor. So during the time when I was. I just started a new job at a startup company, and then I said, all right, went into the BiggerPockets forums. I talked to somebody about how to have the money to be able to just do the project. So we went from there.

[D]

And then during that project, I knew.

[C]

Exactly what this house was going to be, what the target was. So we were expecting about 220 to 225. And then the house that I ended up flipping was pretty much a spitting image of it.

[A]

Well, Chris, we love that you listen to us on the podcast because people can listen all day long, but actually taking action and implementing. And that goes for me, too. I was on bigger stays recently, actually, it was two months ago, and Garrett Brown gave me this advice of this one piece of software I need to try out. Need to try out. And I was like, wow, yeah, that sounds really cool. Did I implement that?

[E]

No.

[A]

I listened to it, but I didn't do it. Well, two nights ago, I finally sat down, I did it. It literally took 10, 20 minutes to actually do this. And I am just in shock that I let the last two months go by without implementing this software. Super cheap, super easy to put together. And so, yeah, everyone can listen. But will you actually take action and try out the things that are recommended to you? So, Chris, you. You did exactly that.

[C]

Yeah, it was. It. It's super scary. But the action is definitely the thing that sets you apart yet, because talking.

[D]

To a lot of other people, I'm.

[C]

In another mastermind group where people are looking to do their first deal, and it's really just not taking the action. Once you get in, you start taking the action, start taking the calls, and start walking houses. It gets a lot less scary, scary. And after you get through those hurdles, for me, it was the first deal, I really got to see how a lot of those pieces moved. You know, finding the houses, running numbers, raising money.

[D]

That.

[C]

It was super scary in the beginning. But then for houses, you know, 2, 3, 4, 5, it was really, you.

[D]

Know, simple to kind of be able.

[C]

To move in from there because you already had everything lined up with hard money. And then it was just, you know, reaching out and networking to More people about the private money to purchase the homes.

[B]

Chris, let me ask a follow up question because I, I appreciate so much what you just said of the first deal. Set me up for the second deal, the fourth deal, the fifth deal, and so on and so forth. And Ashley and I preach that so often that the purpose of the first deal, even though you were in this case, you did have a home run of a first deal, the purpose of that first deal isn't necessarily to have that home run, but it is to give you that foundation. But if we just go back really quickly, because I, I think the piece that I'm still caught up on, that I'm still stuck on, that I think our audience might be stuck on as well, is prior to this, that first deal where you raised money from the Airbnb guy, had you ever raised private capital before?

[C]

No. So I was in college, so that was my first year out of college. And so I originally was looking to be in NASCAR and then do real estate on the side, you know, as a safety net. And so once I graduated college, I got a, you know, a small job in racing and kind of realized that that wasn't going to be the road I took. Moved to a startup company and then, so no raising money, no capital, you know, just trying to be a good person, you know, just being completely transparent.

[B]

But, but Chris, that's even more impressive, right? So you'd never raised capital before, but yet you still went out, you got this property that you couldn't afford to take down by yourself. How did you get past that hesitation or that fear of, well, I don't actually have the money to take this deal down because I think a lot of people can find the deal. I think a lot of people can say, hey, man, this looks like it's going to work out really well. But then once they realize that they don't have the money to do it themselves, they just stop. So how did you break past that obstacle that stopped so many people in their tracks?

[C]

Yeah, you know, listening to all the podcasts and reading the books, they tell you if you have the deal, you're going to be able to find the money. And then you just start going through your contacts. Who would have that, who would have the funds to be able to, you know, invest in the deal?

[D]

You're going to get a ton of.

[C]

No'S, but it only takes one yes to be able to raise the money and be right. And I knew if I just kept reaching out, it's going to lead me to somebody. Maybe it's not that person. But you also add in the text, it's like, hey, I have this opportunity. Would you or someone, you know, be interested with being able to raise the money? You know, it might not be that exact person, but.

[D]

But what we can do.

[C]

Or it might not be that exact person, but when in that text you're saying, you know, if you know somebody else that's going to be able to lead to those other opportunities, because maybe they're in real estate, maybe they know other people looking for those returns, and then they can shoot it out to you. So, you know, just being able to listen and say, all right, I have the deal. I know I can find the money. I'm going to these real estate events. I'm going to be able to find some. Somebody.

[D]

And then, you know, not having a.

[C]

W2 to back you up, it kind of puts your back against the wall and say, hey, you know, I have to figure this out.

[B]

Chris, what about rejection? Because I think that's what most people are afraid of, is that that discomfort or that uncomfortable feeling of reaching out to someone and the. The idea that they might say no. What about rejection? Were you not worried about that?

[C]

Not really.

[D]

Kind of.

[C]

Kind of like I said, you know, when your back's against the wall, it's like you have to do something. So you're going to get a lot of those no's, but it's only going to lead you to a yes. It only takes one yes to be right.

[D]

So, you know, it really, it really.

[C]

Wasn'T the fear of rejection. You know, especially when you start doing cold calls, you know, you're going to get 120 no's, but, you know, it only takes one yes to be able to get a deal done.

[F]

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[E]

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[A]

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[A]

Baselane.Com biggerpockets so Chris, you kind of gave us a lot of insight into raising private money and how that looks for you. But but as you've gone on to do more and more flips, what changed in the way that you actually analyze the flips now compared to when you first started?

[C]

So now you have a little bit of data after doing the first one so you're able to see, you know, what did I spend on that kitchen? Was there any electrical? Okay I know how much windows or, you know, a deck is going to cost. So you have a little bit of data going into that next deal and that was pretty confident. So being able to have a real estate agent who's been in the market for a long time who's able to run those numbers for you, I felt really good about the ARVs.

[D]

So I knew if I could send it to them and you know, just.

[C]

For the safety net, now I know.

[D]

A little bit better.

[C]

I was just taking their ARV and you know, subtracting 10 or 20,000, saying, okay, well this is, you know, about my base case scenario based, the worst case.

[D]

And that I figured out was a little bit wrong.

[C]

But buying that second deal, I said, okay, this is a really good number.

[D]

We know it's going to take quite.

[C]

A bit of renovation to be able to get this complete and with how fast this crew just completed this house and how quickly and you know, efficiently they were able to move.

[D]

You know, I feel really comfortable going.

[C]

Into the next deals.

[D]

So I really didn't have any hesitation on getting the contractor in there.

[C]

He's able to give me a solid quote really quick. And as long as the renovation numbers work with the purchase price, it made sense to me to be able to move forward and buy it.

[A]

And Chris, during this time you're working full time, correctly?

[C]

No, no. So I was full, I was full time real estate.

[D]

So I left a kind of like.

[C]

A lower paying sales job in a startup company. And once my live in renovation was finished, that's when I said, I pulled out the money from the house and said, all right, I got six months to figure it out.

[A]

That's kind of scary as to like even just having that six month Runway as to like really pushing yourself. But I have heard stories where people feel like they were more likely to figure it out because they had, they had to. Like even Tony, when he left his job, you're like, okay, I'm giving myself one year to figure this out and either, you know, I make it or I break it. So what was, tell us just a little bit about what was your plan? Like what role were you inserting yourself as full time real estate investor. So as you know, what would be your role and responsibilities day to day and what did you actually need to do to survive past those six months? Did you have a dollar amount you had to make or a number of flips you had to do?

[D]

Yeah, it was really figuring out the.

[C]

Dollar amount because I was living relatively low. I had a house, I was house.

[D]

Hacking at that time, running out of bedroom.

[C]

So I knew it was right around, you know, four to $5,000, that if I could make that every month, I would be safe. So say I do a flip and make. It takes me four months from beginning to end and I make $20,000. That's $5,000 per month. I said, okay, well, you know, if I can. If I can hit that, that sounds like a really good goal to me. But other than that, it was. I felt like I wasn't, you know, destined to become a W2 worker.

[D]

You know, I was thinking a little.

[C]

Bit outside the box, and it just didn't work very well. Like, I felt very nervous in a W2 compared to being, you know, on my own, saying, hey, it's on me to figure out how to make money, how to move forward.

[D]

And yes, it is very scary. But to me, I felt like I.

[C]

Had no other options. You know, I couldn't go back to another job, leaving two jobs right in a row. So I said, all right, well, you know, I can figure this thing out as a real estate investor and then kind of go from there.

[B]

Chris, so the fact that you were doing this full time, I think, puts more pressure on the success of each deal. And when we talk about renovating and flipping homes, one of the most important things is being able to accurately put a budget together and even more important, being able to. To stick to that budget. So what did you find as a good process? What process did you follow to allow you to have somewhat accurate budgets up front and then do your best to actually stick to those as you moved through the project?

[D]

Yeah.

[C]

So working with the contractor to be able to put those budgets together, because they've done more renovations than me, so they're able to walk into that house, they're able to tell you, hey, this is what it costs.

[D]

We've already done a deal together.

[C]

I felt the connection that we had was really good. So, you know, being able to move forward and say. To block houses together and say, okay, this is how I'm analyzing these houses. So when you're going through, say it's.

[D]

If we need to do everything on.

[C]

The interior, it's going to be about $45 a square foot. So being able to run quick numbers, I can see a house that pretty much needs the interior redone. Nothing absolutely crazy. You know, I'm able to say, okay, well, say it's a thousand square foot house. $45 a square foot. You know, that's a $45,000 renovation. Now, if you're adding anything exterior. They say, that's say if everything in the house needs to be done, it's going to be about 60 to 65,000 a square foot or $65 a square foot. So again, a thousand dollar house, it's probably going to be between a 60 and $70,000 renovation. And then, you know, for bigger houses, that's all you got to multiply. So that's how we were running the numbers and being able to go from there. So I felt pretty confident walking every house with him to say, hey, this is where we're buying it at. You know, what's your cost gonna be? So we were very on the dot when we would walk these houses. And then, you know, when situations come up, that's when it got really rough. And that's where the experience really hurt me because we did did go over.

[D]

Budget and we ran into an unexpected.

[C]

Permitting problems, inspection problems. So for my second deal, you know.

[D]

Where I thought, you know, the first one knocked it out in 12 days.

[C]

We'Re going to be, you know, that 45 to 60 day on a much bigger project. You know, we hit that and it delayed us three months. So, you know, it was a really big learning curve. But you know, the back against the wall, it's like, hey, I got to figure this out. We got to raise more money, we got to do more deals.

[B]

So, Chris, you mentioned delays, right? And I think all of us who have done rehabs have experienced some sort of delay having gone through that. Did that change how you underwrote your future deals? And if so, what changes did you make?

[D]

Yeah, so a lot of these kind of took place at the same time. So. So doing my second deal, I was looking for the next one because now it's like I got one under my belt, I was able to raise money. It's looking for that second, third and fourth deal. So going from there, it's. We had one project going on, we were kind of in the middle of that, then I bought my next one and then I bought another with a, with a partner. So being able to roll into those, it's learning how the money flows. That was a big learning curve for me because what I ended up finding from the partner is that they weren't doing things correctly and mainly on the money side. So they were teaching me how the money flows through the project, how you can kind of survive during this time to where, hey, you have a bunch of flips going, you don't have money coming in. They're saying, okay, well if you Know, you budget an extra 10,000, that's for you to kind of, you know, put back into you. And that's where I figured out that's wrong, you know, if you're not budgeting that correctly. So. And that's where the domino effect kind of started coming from. So doing that project with that partner, you know, I learned a lot about what they were doing and how they were doing business. And I realized, oh, my gosh, like, I've made a lot of mistakes here because now we have, you know, three, four, five flips going on. One or two aren't selling. We're kind of hitting roadblocks. And it, it makes you really take a deep look at what you've been doing for the past six months on these projects and, you know, going forward. And that's kind of what I'm cleaning up right now. So year one was a lot of getting into the game, making a lot of mistakes. So year two is a lot of, you know, damage control, trying to clean up those mistakes so that we can set us up for a really good year three.

[B]

And Chris, I, I appreciate you sharing that because I think your story echoes a lot of what Ashley and I have both experienced experience as we somewhat rapidly scaled up our portfolios. And for all of the Rickies that are listening, when you. When you think about scaling, there's a few different ways that you can scale. You can scale in terms of the actual scope of the project, right? Like, how big of a project are you taking on? And you can scale by just continuing to do bigger scale, right? Like bigger scopes of work on the actual project. So for Chris, maybe the first one was just, hey, we're painting cabinets and, you know, swapping out fixtures. The second one, hey, we're actually redoing kitchens and bathrooms. The third one would be, hey, this is a full gut rehab. We're taking it down to the studs, right? So you can scale in terms of the scope. The next way that you can scale is by the quantity, like by the batch size. So how many deals are we doing at one time? So maybe Chris says, hey, I'm going to continue just to do, you know, these super light cosmetic jobs, but I'm going to do 10 of them at a time, right? That. That's another way to scale. It's just increasing the batch size. And then the other way to scale is the time in between those deals, right? Like, how much time are you giving in between the deals that you're doing? And I think the challenge is that especially as A new investor, and especially when your first deal goes so incredibly well, it can become almost addicting just to keep adding the next deal and the next deal and the next deal. And the challenge with that is that you're not giving yourself enough time to see one of the deals all the way through to take all of those learnings and then apply them to the next one. So, Chris, you mentioned that you had some good learnings, but you were already in the middle of five other projects going on where it would be difficult to go back and apply those learnings. And I think that is where a little bit of patience and a slightly more measured approach as a rookie can actually be beneficial. And we're living this out in our own portfolio right now because we. We launched our hotel about a year. A little over a year ago, so 18 months ago now, and we're still learning today. And I've been hesitant, even though I know we could raise the money, I know that we could find the deal. I know that we could take another one down. I've been hesitant to do that because I'm trying to make sure that I've got enough learnings from this deal that I can make sure that the next deal is a strong enough iteration so I don't find myself in the same position all over again. So all of that to say, Chris, I appreciate you sharing that, but more importantly for our rookies that are listening, don't scale just for the sake of scaling, and make sure that you're giving yourself enough time to learn from the first deal so that you can then apply it to the next deal.

[A]

Now, Chris, you had mentioned that there were some, you know, mistakes that you saw in your partner and lessons learned of things not to do. Were there any red flags that. Looking back as to, like, oh, I should have known this wouldn't be a great partnership based on these red flags.

[D]

You know, I think about that a lot now. So being able to go back through. I think their mindset was more towards rentals and building equity. But it wasn't something that I really saw until we did a project together, because then you're working a lot closer. You know, they're managing the contractors. My job in that was I said, I want to see how you work, how you operate, because you've done a lot more than me. So being able to go through that project and see, you know, see what I like, what I don't like, even if we work well together, that was the main goal of that project. And, you know, you know, the end result Was we don't. So being able to see how they manage the general contractors, I didn't really like that. And then the biggest part was the money, because I started figuring out that they were very, very far off on their numbers and all these flips and projects when we started working together that she was managing or doing herself, they were, you know, disaster projects. So none of these flips were selling. None of the houses were even close on the arv. So when we started looking at. So I started seeing that, and then I started looking at my projects, and I started seeing, oh, my gosh, the ARVs are way off. You know, we're getting into these houses thinking they're $60,000 renovations, because that's what she was telling me and the contractor. And we're getting in there and seeing that it's 80 and 90,000, and then it's hit the oh, no button. So once I kind of saw that and, you know, learn more about their backstory, how they manage money, their personal situation. You know, losing hundreds of thousands for people owing hundreds of thousands, being in, you know, a really, really bad position. You know, you become the five people you hang around. And that was the person I was spending time with every single day. So I was heading directly there. So I shut down everything I was doing and said, I'm not buying again. I'm not raising more money until I, you know, all these pieces stop moving around so I can figure out exactly where I'm at. So now that I've offloaded two of those properties, and now I'm pretty much stuck with two other ones that I'm working on trying to, you know, figure out what to do with them. So being able to see through that process, you know, what exactly they were doing, that was the biggest red flags. And I didn't see that until we, you know, did one together.

[A]

Now, Chris, was that just with your flips, where you really looked and optimized your properties, or was this with all of your properties? Because I know you have some rentals too.

[D]

Correctly, yes. So this was. This was all on the flip side. So, you know, my whole goal was to be able to create active income for myself. So, you know, how can we get into a project and then sell it within six months? And, you know, when your ARVs are, you know, about 30 to $40,000 off, you know, that that impacts that and just keeps kind of putting you in the negative. So this was all flips.

[B]

So, Chris, I totally understand that not every partnership works out the way that we planned for them. To work out. But I guess going back to the beginning of this partnership, where did you guys actually meet and what was that initial conversation like to make you feel that this could potentially be a good partner for you?

[D]

Yeah, so it was right when I, you know, started real estate full time. So I left the normal sales job and then I said, all right, gotta figure it out. I gotta start walking houses. And, you know, this was one of the real estate agents that was, you know, representing the house. They said, hey, I have an open house this day. I saw I was looking for subject to opportunities at the time. And then.

[C]

So walk the house.

[D]

And they said, you know, this was a renovation. It's probably not going to be it, but have you ever, you know, looked into flipping? And I said, no, I'm. I'm really just looking to. For the expired listings. And they said, well, you know, it's like I have a couple flips going on, you know, that's might be something you're interested in. And she said, the one thing I can't get to right now is the expired listing calls because she's a realtor. She said, you know, if they're, you know, if you can work something out with them to buy a deal from them, that's great, but, you know, if they're looking to relist, you know, you can just shoot them over to me. So that's how I started working with this person and then I started walking their projects.

[B]

So you guys had built a relationship and it felt like that there was maybe some. Some skill set there that would make it beneficial. But I do think that's part of the challenge of partnerships and why it's always good to start on a smaller scale, I guess. Chris, my last question, the partnership piece, how many of the flips that you guys had done together actually sold before you added the next one? Like, did you. Did you do a full deal together and say, oh, man, this went incredibly well, and then you guys did another one and another one, or was it like, hey, let's go scoop up like five at one time. And ncl, all five of them, them go, yeah.

[D]

So there was a lot of trust built up. So, you know, we were communicating every day. So she helped me buy my first one was the agent, you know, confirmed all the renovation numbers, sent me contractors, and then I did. I bought two more within that time frame before we did a project together.

[B]

And did you complete that first project all the way through? Like the one where you guys were actually partners on? Did you complete that one all the Way through before doing the second one together.

[D]

So we didn't do a second one together.

[C]

That was the one.

[D]

Yeah, yeah. So it was.

[C]

When I say it was a disaster, it's a disaster.

[D]

So we're still working through that and about to head to court for it now, so.

[B]

Yeah, but, but Chris, I, I think that's the point that I was trying to make is that starting small on a partnership is sometimes the best way. And, and you can start small by buying properties that are less expensive. Flipping, I think, is a great way because typically there's an in and out period. Right. Like it's a little bit more defined than owning a rental together. But even with all of those, sometimes it's hard to kind of pick the right partners in the wrong one. So, Chris, I want to get into more of your story and I think every Ricky listening just got a masterclass in how partnerships can either make or break your business. And fortunately, you can check out the book Real Estate Partnerships that Ashley and I wrote together where we break down our experience in real estate partnerships. Now, Chris, when we get back, we want to hear more about your story and what's happening next. And we'll hear that right after a word from today's show sponsors.

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[B]

All right guys, we're back here with Chris. Now. Chris, you said that you want to restart clean, right? And you mentioned that before the break, but what does that actually look like for you right now?

[D]

Yeah, so like I said, some of the pieces have stopped moving now, so I've been able to kind of really figure out where I'm at. Yes, it's negative, but being able to find the roadmap to, you know, be able to get out of it. So I'm in a new kind of community here locally so that, you know, they do tax, legal, bookkeeping and operations all under one roof. So it's something new. And we're getting really, really hands on and one on one coaching from these people who are doing lots of deals. One of the bigger name attorneys down here in North Carolina so they're able to Kind of coach me through, you know, where to go from here. So what that looks like is I have one house on the market right now. I have two projects left that I'm looking to raise money for to be able to finish the projects. So restructuring some of the private lending partnerships has been a big part of that because, you know, for me, you know, creating those good relationships, I've been able to go to them and I've been giving them weekly updates on the projects. So that kind of builds that trust. They know exactly where I'm at and, you know, we can hop on a call if anything goes wrong. So when it has gone wrong, I've been able to hop on a call and say, hey, this is the situation. I understand exactly where I messed up and here's how I'm getting out of it. So they're all, they're all on board and, you know, figuring out how to help me because they're like, hey, you know, this is, this is where we're at. We're trying to, you know, help you through this as well. So restructuring the money, finishing these two projects, and then, you know, kind of like Tony said, how are we slowly trying to build back up now that.

[C]

We'Ve made the mistakes?

[D]

I'm not going to go buy five projects all at once. You know, I've learned so much through what's gone wrong to where, you know, I feel a lot more confident now that, you know, I know what a good deal looks like. I'm connected with a lot better people. I have a rockstar agent now. I'm connected to a lot better contractors who these people are sending me. And, you know, we're able to walk houses a lot more confidently. So being able to finish those two projects and then be able to start, you know, slowly buying flips again. And then on the side of that, we just turned our, my first house into a medium term rental. So that's booked out for the next 45 days through Airbnb. And then we just bought the house that I'm in, a new primary subject too. So super excited about that.

[A]

Well, Chris, before we close out here, I want to hit you with some rapid fire for a little advice for our listeners today. So first of all, what's the one thing that you are most proud of so far in your investing journey?

[D]

Being able to get started. I'd say, you know, coming out of a normal sales job or even a W2, it's really, really scary from the outside, but being able to get in and take the action, you're going to be steps and leaps and bounds ahead of anybody else who's just listening to podcasts, still reading the books, you know, because I've been meeting people that have been doing that for years and they still haven't taken that action. So being able to take action when you really don't have another way out has been the thing that I'm most proud about.

[B]

What would you say has been the biggest rookie mistake?

[D]

Oh, man, there has been so many of them. But, you know, ton, tons of mistakes along the line. I probably couldn't highlight a single one. But, you know, you're learning so much more through your mistakes than anything that goes right? Yes, I learned some things on that first project that went as perfectly as you could imagine. But, you know, I'm learning so much more about what's on the things that have had, have been going wrong that I wouldn't trade that for the world. Because when I get out of this little hole, I'm going to be able to accelerate so much quicker with better connections, better numbers, and a lot more trust with people around me.

[A]

Chris, if a rookie wants to flip their first house this year, what is one piece of advice you'd give them?

[D]

You got to be able to start walking houses. Because if you're not taking action, if you're not calling agents saying, hey, do you have any houses that need some work? If you're not talking to wholesalers, if you're not going to real estate meetups, you're never going to be sent those deals. You know, if you get out and start networking with these people, start calling agents, you're going to be connected to something. You know, a lot of those numbers probably aren't going to work, but as long as you're, you know, taking action, making the calls and start walking houses, you're going to be able to get started.

[B]

What's one way that a Ricky can copy the successful model of other successful real estate investors in their market?

[D]

Being able to go to the meetups and basically shadow them, send them deals, send them opportunities because you're bringing value to them. Because if they're an investor doing high level flips, they're going to be able to show you exactly how they're doing it. They're going to be able to show you the numbers, they're going to be able to connect you with, you know, agents, lenders, whoever you need in contractors. You know, your network is your net worth. And I really learned that through this process. So get out there and, you know, find people that are doing it at a high level and just copy everything they're doing.

[A]

Well, Chris, thank you so much for joining us today. We've really appreciated having you on as a guest today to share your knowledge and your experience. Where can people reach out to you?

[D]

Yeah, you can follow me on Instagram and TikTok at Chris Rickenbaugh. That's chris.r e I C H E N B A C H and you can follow along on my journey on my podcast, the Leadway Wealth Builders podcast, where I document from quitting my job all the way through now. So follow me there.

[A]

Chris, thank you so much for joining us today. Everyone else, thank you so much for listening to the Real Estate Rookie Podcast. I'm Ashley, he's Tony, and we'll catch you guys on the next episode.

[B]

Hey rookies, if you're watching this, we want you to apply to be a guest on the Real Estate Rookie Podcast. That's right. Ashley and I are looking for amazing stories just like yours to be a part of our Real Estate Rookie Podcast. Now look, you don't need to be an expert. You don't need to have done thousands of deals. Even if you've done one deal, your story could help inspire the next listener.

[A]

As a rookie investor, especially if you just got your first deal, it is all fresh in your minds and you are the best person to tell your story, give your experience on how you got it done to help someone else get their first deal.

[B]

So head over to biggerpockets.com guest if you want to be a part of our show again. That's biggerpockets.com guest and we'd love to have you on.