Don’t Rush the Climb: Real Estate Lessons From 40+ Flips and Long-Term Growth
Show summary
In this engaging interview, real estate expert Ryan Gifford shares his journey from starting in real estate during the recession to becoming a successful investor and agent. Discover his insights on discipline, adaptation, building relationships, and taking small steps toward big dreams.
Key takeaways
- Ryan Gifford has owned and flipped over 40 homes and started during the recession, when his first flip took 7 days to sell, which he now considers fast given market conditions at the time.
- His business today covers rentals, flips, and agent work helping clients buy starter homes, dream homes, and sell properties.
- He credits his mom's background flipping properties and his own earlier design company (designing condos, houses, townhouses) for teaching him how to see a property's potential rather than its current condition.
- He describes discipline as non-negotiable for surviving in real estate long term, and says the career forced him to adapt to different environments and social settings.
- He treats client relationships as friendships: during a 30-45 day transaction he expects to be in constant contact handling lender issues and calming nerves after inspection reports.
- He is currently negotiating a new flip deal and developing land on the west side of Winston-Salem, planning to build houses and convert any unsold units into Airbnbs.
- His core advice to investors chasing big goals: set ambitious dreams but pursue them one step at a time, since moving too fast risks a setback that leaves you worse off than when you started.
In this episode
- 02:08Introduction to Ryan Gifford
- 03:20Origin story: starting in real estate during the recession
- 04:57Early influences: mom's flipping background and design company
- 09:19What the journey has taught him: discipline and adaptation
- 13:27What's next: current flip deal and land development project
- 14:33Relationships as friendship with clients
- 16:57Closing message: take small steps toward big dreams
- 18:30How to connect with Ryan Gifford
About the guest
Ryan Gifford runs Gifford Realty LLC in Winston-Salem, North Carolina. He has owned and flipped over 40 homes, started in real estate during the recession, and works in rentals, flips, and as an agent helping clients buy and sell homes. He has a design background, having previously run a design company doing condos, houses, and townhouses, and is currently working a flip deal and a land development project on the west side of town.
Listen to the audio
“I think when people tell you to shoot for the stars, the folks that run too fast up the staircase is going to trip and fall and fall back down. But the people that took one step at a time getting up, they're still in the center of that staircase taking their steps going up.”
Ryan Gifford
“As an agent, we've got to become their friend. We have to look at them not as a paycheck, but as an individual who's needing the guidance and needing that friendship at that moment from us.”
Ryan Gifford
“Time is something we have. And we need to use that.”
Ryan Gifford
Questions answered in this episode
How did Ryan Gifford get started in real estate?
He got his real estate license after moving to North Carolina, starting during the recession when getting a loan was hard for buyers. His first flip during the recession sold in seven days, which felt long at the time compared to how fast his properties sell now.
What is Ryan Gifford's business focus today?
He works in rentals, flips, and as an agent helping clients find dream homes or starter homes, and helping people sell their homes. He personally enjoys buying houses and improving them, using his design background to help clients see a property's potential rather than its current state.
What advice does Ryan Gifford give to new real estate investors?
He advises setting big dreams and ambitions but pursuing them one step at a time rather than rushing. He compares it to running too fast up a staircase and tripping, versus taking steady steps that keep you moving upward without falling back to the start.
How does Ryan Gifford view client relationships as an agent?
He describes relationships in business as friendship. During a 30-to-45-day transaction, clients call constantly with lender issues or concerns from inspection reports, and he says an agent has to calm their nerves, explain things repeatedly, and treat them as a person needing guidance rather than just a paycheck.
What is Ryan Gifford currently working on?
At the time of the interview he was negotiating a flip deal he hoped to put under contract, and he had land on the west side of Winston-Salem where a road was being put in so he could build houses, with a plan to convert any unsold properties into Airbnbs.
Where is Ryan Gifford based and how can investors reach him?
He is based in Winston-Salem, North Carolina, and runs Gifford Realty LLC. He shared his phone number, 336-971-6705, and said he's happy to talk through real estate or design questions, including giving feedback on paint colors, even with people from a distance.
Resources and links
- Ryan Gifford’s Website
- Ryan Gifford’s Phone Number: (336) 971-6705
Full transcript
Ryan Gifford (00:00)
I think the message is to follow their dreams, but to do it one step at a time. Because I think when people tell you to shoot for the stars, the folks that run too fast up the staircase is going to trip and fall and fall back down. But the people that took one step at a time getting up, they’re still in the center of that staircase taking their steps going up. I definitely think to
Set your dreams, set your ambitions, and take the proper steps to get there.
Quentin (02:08)
Hello everyone. Welcome to the Real Estate Pros podcast. I’m your host Q Edmonds and I’m excited to be here today. I have another fantastic guest here and I just cannot wait for us to kind of see things from his lens. This gentleman has owned and flipped over 50, over 40 homes, has a design background, has a mindset that thinks like a farmer but acts like a wolf.
And hopefully he’ll expand more on that because I never heard that before, but I love it. I love that. And so I’m so excited for us to get to learn more about Mr. Ryan Gifford. Mr. Ryan, how you doing today,
Ryan Gifford (02:49)
Well, how are you?
Quentin (02:51)
man, doing good sir, doing good. I’m so glad that you’re here. And listen man, I am the type. I like to dive right in. So I would love for you to tell the people what’s your main focus these days. If you don’t mind, Mr. Ryan, us a little bit of our origin story, kind of how you got to where you are now, and then tell them what part of the world you’re in. People love to know where you are geographically. So what you’re up to, your origin story, and where you are. Mr. Ryan, sir, you have the floor, my friend.
Ryan Gifford (03:20)
Okay, that’s a lot packed into a question. am in North Carolina, Winston-Salem, ⁓ Cigarette City, also known for Krispy Kreme. ⁓
Quentin (03:24)
Yeah.
Ryan Gifford (03:36)
I… my story. I started real estate during the recession.
We focus on multiple things. We do rentals, flips, help people find their dream home, help them find their get-buy home, help them ⁓ sell their homes. I personally, when I’m not selling real estate, I like to invest in property. ⁓ I enjoy…
buying houses, making them into something great that somebody would like. ⁓ Fortunately, that’s something I have a knack for.
And when we’re selling houses, I can help my clients look at a property and see what it can be, not what it currently is.
Quentin (04:47)
Love it, man. Thank you, sir. Appreciate it, man. How did you kind of get into this space? What inspired your passion for real estate,
Ryan Gifford (04:57)
Multiple things. ⁓ Growing up, my mom ⁓ flipped properties. That was her thing. ⁓ And you know, I’m a Gen X or so, we worked. We didn’t have a choice. And it didn’t matter what you did, you were told to do something and you helped. Everybody helped out and everybody worked. ⁓
Quentin (05:06)
Gotcha. Yeah.
Yeah. Yeah. Yeah.
Ryan Gifford (05:24)
So, you know, that gave us our
first, my first insight to things ⁓ and seeing how the gears and the wheels worked on it. ⁓ From there, I went and we opened a design company and I was designing these condos, houses, townhouses, all kinds of places. And it was my ideas that was making
a lot of money for these people. ⁓ And yeah, they would ⁓ put my ideas into motion, but without the idea, there would be no motion. ⁓ So after I moved to North Carolina, that’s the area I decided to dive into. So I went and obtained my real estate license. ⁓ And, you know, during the recession, selling a house was tough.
Quentin (06:43)
Mm-hmm.
Yeah.
Ryan Gifford (07:12)
⁓ Because, you know, nobody could get a loan. If they could get a loan, had, they were a dime a dozen. They could choose from whatever they wanted. ⁓ So I did what I knew how to do. I bought a flip in the recession. ⁓ And I sold it in seven days. So, which now seems like a long time, because usually mine sell within a day or two. ⁓
Quentin (07:37)
Right. Yeah.
Ryan Gifford (07:40)
But seven days in the recession, looking back, I was super fortunate ⁓ for that to have happened. And from there, everything just…
snowballed, which is good.
Quentin (07:56)
Yeah. I love it, man. Thank you, sir. Thank you, Mr. Ryan, man, for walking us through the journey, letting us know what you do, kind of how you got into this space. I’m going to do a brief summary of what you said. I’m an active listener. So as you was talking, I was writing, because I love making this statement and then asking you a question after the summary. So you started on real estate during the recession.
You know, did rentals, flips, help people get into their dream homes, help people buy their get by homes, you know, they’re stepping stone until they get to their dream home. Definitely enjoy buying houses, helping clients, helping them see what can be, right? Not just what is, what can be. And so, you know, your mom flipped properties, she was a Gen Xer. So, you know, you had that mindset to work. You had to do something. So you had that mindset to work.
And man, once you started working, know, the gears started kind of turning. You was helping people make money on their homes. But like you was like, OK, I’m helping them, but they got to be more to this. And so, you know, you moved in North Carolina, got your real estate license and things just been kind of like wheels been turning and things just been working out for you. That pretty good brief summary right there, Mr. All right. Love it. Love it. And so we know, you know, life.
Ryan Gifford (09:15)
Yes, sir.
Quentin (09:19)
Even though you gave me that quick synopsis and maybe like three or four minutes, we know that everything within that three and four minutes did not unfold in three and four minutes. was, it was life happening over time. Right. And so Mr. Ryan, I have a statement that I make. say destiny has no wasted moments, right? Destiny has no wasted moments. And that just means that we’re borrowing from each journey of of our, of of our walk of each, each.
Ryan Gifford (09:43)
you
Quentin (09:47)
Each season of the journey, we take something and it refines us. It refines our mindset. It refines our systems. It helps us zero in on what’s working, what’s not working. And so Mr. Ron, I would love to know throughout your journey, the transition going to North Carolina, throughout the journey, what has it taught you about yourself? What has it revealed to you? Has it revealed discipline? Has it revealed… ⁓
Ryan Gifford (09:49)
you
you
Quentin (10:14)
Has it made you humble? Has it changed your outlook on innovation? What has the journey taught you about you, Mr. Ryan?
Ryan Gifford (10:58)
Well, mean, in order to be in real estate, successful and to maintain and stay into real estate, you have to be disciplined because there’s no other way. ⁓ If you don’t, you don’t survive. ⁓ I’ve grown as a person because, you know,
aside from age and maturity, ⁓ it’s taught us.
to learn to adapt ⁓ and yeah, to adapt to different environments, different social settings, different everything. ⁓ And it gets you out of your shell. And I think that as a person was what I needed. ⁓ And so the career helped me evolve in that
Quentin (12:01)
Yeah.
Ryan Gifford (12:02)
And I’m grateful for it. I’m grateful for the good times and the bad. Because if I didn’t have the bad, wouldn’t be able to appreciate the good. And I’m super grateful for that.
Quentin (12:15)
So well said, man. If you didn’t have the badge, you wouldn’t appreciate the good. You know, I’m learning what actually grows us, what makes us stronger, is actually holding the tension, right? Like if we go to the gym, if we lift weights, that’s what actually helps you define your muscles is holding the weight, holding the tension, right? If you never lift the weight, never lift the tension and hold it, you don’t develop. And so, you know, even in life,
once we’re going through just the ebbs and flows, holding attention is what actually develops us. So I love how you said, you know, taking it good with the bad, because you’re right. That develops us into the round, the rounded person we are. My wife has a saying, and I don’t know where she got it from, but she says, a calm sea never makes an experienced sailor.
Ryan Gifford (13:05)
Yes.
Quentin (13:05)
A calm
sea never makes it spin. You got to have the waves. You got to have times when you drop the wave, know, drop the sail, when you put the sail up, when you adapt, drop anchor, put up anchor. Like you have to have those moments. And so I love it, man. So let me ask you this, Mr. Ryan, what’s next for you, sir? What’s next for the business? What are you looking to solve or scale next? Like what’s next for you as a businessman?
Ryan Gifford (13:27)
⁓
I’m currently negotiating a deal that I hope to close well that I hope to go under contract today ⁓ for a flip property and I have some land that is on the west side of town that I’m going to be developing here within the next week they’re putting in the road and we’re going to
build some houses there, ⁓ get that done and see where that leads us. And if they don’t sell, they’ll be Airbnbs.
Quentin (14:08)
Yes, sir.
I love it, man. I love it. ⁓ Mr. Ryan, I always love to get people’s unique perspective on this word. So when you hear the word relationship, what rings true to you within business? The word relationship, what comes to mind for you,
Ryan Gifford (14:33)
friendship.
Quentin (14:34)
Mmm. ⁓
Ryan Gifford (14:36)
Yeah. When you’re working with a client, you become their best friend for the next 30 to 45 days. They call you morning, noon and night. They have issues with lenders most definitely. Then they get their inspection report. Of course, they’re not happy. No one is. But it’s the inspector’s job to find things. ⁓ And as an agent, we have to…
calm the nerves, we have to talk to them, we have to explain things to them. And oftentimes it’s multiple times because people hear and see what they want to hear and see.
And as an agent, we’ve got to become their friend. We have to look at them not as a paycheck, but as an individual who’s needing the guidance and needing that friendship at that moment from us. so for me,
I would say a relationship is a friendship.
Quentin (16:22)
I absolutely love that my friend relationship as a friendship. I absolutely love that man. ⁓ Listen, man, this is such a good conversation. Let me ask you, sir, ⁓ is there any topic that I have not brought up that you would like to talk about? Is there any other words of inspiration, education or motivation that you would like to leave with the people? Like maybe you came in with a
a message in your head, in your heart. I just want to make sure that I leave space for you to kind of land that message if you have it.
Ryan Gifford (16:57)
I think the message is to follow their dreams, but to do it one step at a time. Because I think when people tell you to shoot for the stars, the folks that run too fast up the staircase is going to trip and fall and fall back down. But the people that took one step at a time getting up, they’re still in the center of that staircase taking their steps going up. I definitely think to
Set your dreams, set your ambitions, and take the proper steps to get there.
And don’t try to run too fast to get there because if you do and you trip and fall, you’re going to be left in a worse spot than what you started in because not only are you back where you started, but you’re also going to be injured in some type of way. So I guess the best advice is to just take the steps.
and make the small steps in life. ⁓ Because you will eventually get there. And it may not be at the speed you want. But the thing is, time is something we have. And we need to use that.
Quentin (18:11)
Yep. Sir, I appreciate you, man. This was great. You’ve given us some really good nuggets to think about. If someone wanted to reach out to you, connect with you, collaborate with you, learn more about what you’re doing, how can they get in contact with you,
Ryan Gifford (18:30)
⁓ well, I’m Ryan Gifford and my real estate company is Gifford Realty LLC in Winston Salem, North Carolina. ⁓ my phone number is 336-971-6705. I ⁓ am definitely a talker. ⁓ somebody calls me, I’m picking up that phone cause I’m a gabber man. We’re going to talk and get it out of the way.
Quentin (18:57)
you
Ryan Gifford (19:00)
⁓ But also I don’t mind helping somebody even from a distance ⁓ and talking them through things so I’m completely fine with that. If they have a question, if they want to bounce something off of me, I get a lot of color requests. Somebody sends me a color and says, how would this look? ⁓ So the thing is like I said, I’m open to whatever.
Quentin (19:19)
Yeah.
Ryan Gifford (19:28)
whether it’s real estate, they want some design advice, I’m cool, we can work with it.
Quentin (19:34)
Yeah. Well, listen, Mr. Ryan, sir, let me say three things to you, ⁓ First, thank you for your time. I appreciate you coming on and giving us your time. I think time is our most precious commodity. So I appreciate your time, Secondly, thank you for your story. Thank you for coming on and sharing your perspective, your experience, your life experience. ⁓ I think stories and narratives, our stories, have a way of planting seeds into people. And we may never see the growth.
And we don’t know when the growth is going to take place, if it does. But the seed is there. And so I thank you for coming and planting seeds today. And lastly, man, thank you for your mindset, sir. Thank you for the way you think and bringing that mindset to this platform. I greatly appreciate you coming on today,
Ryan Gifford (20:05)
We done.
Well thank you, I appreciate you having me.
Quentin (20:18)
Absolutely. Well, listen, y’all heard Mr. Ryan. Look into the show notes, get in contact with him, but definitely make sure you’re subscribed here because I promise you we’re going to continue to bring up amazing people just like Mr. Ryan. So, sir, I say thank you again and everyone else. Y’all have a fantastic day.
Ryan Gifford (20:33)
Thank you.