Hustle Humbly Podcast

Alissa Jenkins & Katy Caldwell

Join us for Hustle Humbly where we hope you will build the confidence to find your voice and your way to a successful real estate business and beyond. Listen in as Alissa & Katy, two top producing Realtors, talk about fostering community over competition while navigating the often times cutthroat real estate industry. With over 1000 homes sold between them and 13 and 19 years each in the business, they have seen it first hand. Deep dive into conversations and interviews about mindset and best practices with real life stories mixed in. The goal of Hustle Humbly is to reach out and encourage Realtors and business people alike to stop comparing themselves and start embracing their own strengths.

  1. 16h ago ·  Video

    364: How to Handle Losing a Client

    You win some, you lose some. So why does losing one always feel like it means so much more? This week we get into what happens after the deal falls through, the client picks another agent, or a friend quietly lists their house with someone else. We talk about the "one day rule" a friend taught us for grieving a lost deal, and why real estate karma means the good and the bad even out over time if you let it. We share the moment a nervous friend told us she wasn't hiring us, and why we've learned to respond with grace instead of guilt-tripping. We get into the client who broke the news she was moving out of state over text, the ones who ghost instead of confronting you, and why the people who face you directly deserve to never regret it. We also cover the awkward reality of splitting business between two agents in one household, the ChatGPT trick for cooling down an angry email before you hit send, and a listener's story about a "shopper" who keeps circling back without ever committing. Then we tell the story of a seven figure deal that turned into a $70,000 condo, then into no deal at all, and how walking away with honesty turned into a stream of referrals instead. And we close with the story of an eight year strained friendship that got repaired with one honest text message. Here's what we cover in this episode: Why we believe in real estate karma and how it evens out over time The "one day rule" for grieving a lost deal and moving on What to say when someone nervously tells you they're not hiring you Why business gets messier when it's built on relationships, not just transactions The client who confessed she was relocating out of state over text Being the icebreaker when a client lists with someone else and never tells you How to handle it when a buyer's spouse already has "his" agent Splitting a household's business between two different agents Using ChatGPT to turn an angry email into a professional one A listener's letter about a shopper who never quite commits Sticking to your boundaries even when it might cost you the deal The seven figure deal that shrank to a $70,000 condo, then to nothing How honesty about a bad purchase turned into new referrals Repairing an eight year strained friendship with one text Our rapid fire list of real estate karma quotes to remember Key Quotes & Takeaways: "Be the agent who says no worries, I'm happy for you, and actually means it." "Every time you choose grace over resentment, you're playing the long game." "Don't burn a bridge because you're hurt. You may need to cross it again later." "Real estate is hard enough without carrying a backpack full of grudges." "If you take every business decision personally, this business will eat you alive. Your value is not determined by whether someone hires you." "We're building a reputation, not collecting scorecards." Products, People & Previous Episodes Mentioned: Episode 346: Desperate Agent Behavior (hustlehumblypodcast.com/346) Hustle Humbly Community (hustlehumblypodcast.com/membership) Leave us a review at http://ratethispodcast.com/hustlehumbly   Get your FREE Database Template: http://hustlehumblypodcast.com/starthere   Email Templates 101: http://emailtemplates101.com   Agent Systems 101: http://agentsystems101.com   All Resources: http://hustlehumblypodcast.com   Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

  2. Jul 20 ·  Video

    363: What to Do When the Appraisal Comes In Low

    Three low appraisals. Ten days. One Realtor who used to be an appraiser herself, with a dad and sister still in the field. If you've been hearing agents in your market say appraisals are coming in low right now, you're not imagining it. In this episode, Alissa walks us through three real, current transactions where the appraisal came in under contract price, and what she actually did about each one. From a $20,000 gap that took two hours of dispute writing to a $55,000 shortfall that made her question her entire career, this is a real look at what it takes to fight for your seller, or protect your buyer, when the number comes back low. We get into why appraisers are often behind the market, what actually goes into a strong appraisal dispute letter, why you should never let ChatGPT write the whole thing for you, and how to keep your sellers grounded without ever making promises you can't keep. Here's what we cover in this episode: Why appraisals are coming in low right now, and why appraisers are always a little behind the market Case Study #1: the $20,000 low appraisal that got resolved for a $13,000 gap Exactly how to start an appraisal dispute (and why you review before you call your seller) What actually goes in a dispute letter: facts only, no feeling words Why you can't rely on ChatGPT to write your dispute for you Buyer and seller options when an appraisal comes in low, and who really has to sign off Case Study #2: the small $3,000 gap where the seller chose not to dispute at all Case Study #3: the $55,000 appraisal gap that took two of the longest dispute letters of the week How to set your sellers' expectations at the listing appointment so a low number doesn't blindside them Why you're just the messenger with data, and how to keep that from feeling personal Key Quotes & Takeaways: "It needs to be written as factual. Only the facts." – Alissa "You have to know these houses. If the appraiser makes a mistake, the computer doesn't know it's a mistake." – Alissa "You're just a messenger with data." – Katy "It's not that I'm not confident. It's that I know a second appraisal could come in lower too." – Alissa Products, People & Previous Episodes Mentioned: ChatGPT / AI tools (referenced as a starting point for reviewing an appraisal, not a replacement for agent fact-checking) Got a toast for someone who's helped you in your business? This episode's toast is from Samantha Gonzalez, honoring her mentor Teena Marie Mateo. Send yours to team@hustlehumblypodcast.com and we might read it on the show! Leave us a review at http://ratethispodcast.com/hustlehumbly   Get your FREE Database Template: http://hustlehumblypodcast.com/starthere   Email Templates 101: http://emailtemplates101.com   All Resources: http://hustlehumblypodcast.com   Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

  3. Jul 13 ·  Video

    362: Why Buyers Are Struggling Right Now

    You want to buy a house. But you can't. Or it's just really, really hard. We've both got buyers right now who are struggling, and it's not because they're not trying. It's because the math has changed. Back in the 60s, 70s, and 80s, houses were $20,000 to $40,000 and you needed 20% down. Now that down payment number is basically what a whole house used to cost, and the median price in our market has nearly tripled since one of us started selling real estate in 2005. So in this episode we're getting into what it actually looks like to help a buyer who is priced out, unsure, or just starting to gather their numbers. From lender grant programs you may not know exist, to the buyer consultation questions that save everyone time, to the client who thought they had a million dollars covered and didn't, we're sharing the real stories behind helping buyers navigate an affordability crunch without losing hope (or your sanity). Here's what we cover in this episode: - Why the math is so different now than it was even ten years ago - Why you need more than one go-to lender, and how to find out what specialized or grant programs are available in your market - The Regions Bank 100% doctor loan and why niche lender programs matter - A real buyer consultation story and why starting with the numbers first changes everything - How to handle a referral when the buyer's expectations and budget don't match reality - What a credit re-score is and why it matters for buyers who aren't quite ready - The overconfident buyer story that still makes us wince - Why "congrats on your pre-approval" doesn't mean go start showing houses - Why you always need to see a house with your own eyes before writing an offer - How to manage parents who show up excited (and a little too opinionated) during a buyer's search - Why some inspection issues are dealbreakers and others just need a little imagination Key Quotes & Takeaways: - "It's not that I'm too good for the price point. It's that I know the mental toll." - "There's no secret. There's no secret foreclosure. There's no secret fixer upper." - "I just want my buyers to have the information and the education to make a good, sound decision. I don't want the decision made off of emotions or fear." - "Owning the house fixed my credit. Every month I paid that mortgage, my credit just went up, up, up, up." - "You have to start somewhere. It's an investment." (Speaker unconfirmed on all quotes above, this transcript's labels all read "Unknown" instead of Alissa/Katy.) Products, People & Previous Episodes Mentioned: - Episode 361: Agent Vendor Relationships (hustlehumblypodcast.com/361) - Hustle Humbly Community (hustlehumblypodcast.com/membership) Want to toast someone on the show? Send us a voice or video message with your name, who you're toasting, and why! Email it to team@hustlehumblypodcast.com. Leave us a review at http://ratethispodcast.com/hustlehumbly Get your FREE Database Template: http://hustlehumblypodcast.com/starthere Email Templates 101: http://emailtemplates101.com Agent Systems 101: http://agentsystems101.com All Resources: http://hustlehumblypodcast.com Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com Music: Straight A's by Connor Price → https://connorprice.shop/ The Good Life by Summer Kennedy → https://soundcloud.com/summerkennedy/the-good-life Be The One by Matrika → https://uppbeat.io/t/matrika/be-the-one

  4. Jul 6 ·  Video

    361: Agent Vendor Relationships

    Has a lender ever given you the full court press and you weren't sure how to say no? Or maybe you've wondered why your vendor partners aren't sending you more leads? This episode is going to give you a lot to think about. We've been getting messages from agents on both ends of this spectrum — some wanting to know how to get lenders to back off, and others wanting to know how to find a lender who will send them referrals. So we decided it was time to address both, and we're not holding back. We start by going back to basics with a law you may have heard of but probably don't know as well as you think: RESPA, the Real Estate Settlement Procedures Act. It has been around since 1975, and it is still federal law, and it still applies to you and every vendor relationship you have. Then we get into the real conversation — mindset, professionalism, how to say no gracefully, and why expecting leads from your vendors is a trap that will make you miserable. Here's what we cover in this episode: - What RESPA actually is and what it prohibits (spoiler: a lot of what you see happening in the industry) - The history of RESPA, Dodd-Frank, and the CFPB and why these rules exist - Why "things of value" from vendors — including gift cards, event tickets, and subsidized marketing — are considered illegal kickbacks - What co-marketing with a lender is allowed to look like vs. what crosses the line - Why lenders get more aggressive when the market slows and how to handle it with kindness - How to professionally say no when a vendor won't stop pursuing you - Why you should never choose your lender based on what they can do for you - The mindset shift you need to stop expecting referrals from your vendor partners - How to add vendors to your database and treat them like people, not a lead source - A real community story about a lender who finally sent a referral after 16 months — and why it worked - How agent behavior is observed by every vendor you work with, every single time This is your reminder that your vendor relationships are a reflection of your professionalism. And your business is yours to run. Key Quotes & Takeaways: - "If you are an agent out there, you do not pick your lender based on who can do the most for you. We are here to represent our clients." Katy - "The lenders that I use are answering their phones because they're at their office." Katy - "You are being observed." Katy - "I am in charge of what I make." Katy - "Everybody's nice until they're not — until they don't get what they're expecting." Katy - "You are responsible for yourself. You are responsible for generating your own business." Katy - "I want to be known as someone you do not ever have to ask to pay for anything for her, because she's not gonna let you." Katy Products, People & Previous Episodes Mentioned: - The Big Short (2015 film) - RESPA — Real Estate Settlement Procedures Act (1975) - Dodd-Frank Act (2010/2015) - Consumer Financial Protection Bureau (CFPB) - Hustle Humbly Community (hustlehumblypodcast.com/membership) Want to toast someone on the show? Send us a voice or video message with your name, who you are toasting, and why! Email it to team@hustlehumblypodcast.com. Leave us a review at http://ratethispodcast.com/hustlehumbly Get your FREE Database Template: http://hustlehumblypodcast.com/starthere Email Templates 101: http://emailtemplates101.com Agent Systems 101: http://agentsystems101.com All Resources: http://hustlehumblypodcast.com Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com Music: Straight A's by Connor Price → https://connorprice.shop/ The Good Life by Summer Kennedy → https://soundcloud.com/summerkennedy/the-good-life Be The One by Matrika → https://uppbeat.io/t/matrika/be-the-one

  5. Jun 29

    360: Feel-Good Stories from the Field: How to Co-op Well

    The market is tough, agents are stressed, and claws can come out. We get it. But being a jerk isn't going to make anything better, and this episode is our loving reminder of that. We are deep in summer and we just needed a little happy boost around here. So instead of another finger-pointy episode about what's going wrong, Katy and I sat down to share some genuine feel-good stories from the field. Stories about what happens when Realtors actually choose community over competition, even when the market makes that harder than it should be. This episode is the pep talk you didn't know you needed. Whether you are the listing agent, the co-op agent, the broker, or just someone who has been on the receiving end of a kind gesture, we think you will walk away from this one feeling a little lighter and a lot more inspired to be the agent people actually want to work with. Here's what we cover in this episode: How Alissa organized a "speed dating" listing tour with five agents she barely knew and what happened next Why reaching out to strangers in the MLS is not as scary as you think it is The story that went viral-ish: when the agent who lost the listing brought the buyer What to do when you lose a competing listing appointment to a friend Why being the thoughtful co-op agent who calls about the AC or the hole in the ceiling actually matters How listing agents can show up for buyer agents (and why it pays off) The LSU baseball ball signed by a retired player and why a Realtor friend made it possible What happens inside a luxury neighborhood when competing agents decide to run open houses together Why how you exit a brokerage matters just as much as how you enter one What brokers can learn from being gracious when agents leave If you have been feeling the pressure to compete instead of connect, this is the episode for you. Your reputation is one of the best tools you have, and being a good co-op agent is one of the fastest ways to build it. Key Quotes & Takeaways: "Being a jerk isn't going to make anything better." Alissa "In multiple offer situations, your reputation is one of the best tools you can have." Katy "You get more flies with honey." Katy "How do you want to be talked about? That agent is going to go to their new company and they're going to talk about you." Katy "People are starving for the good. We are just not sharing enough of it." Alissa Products, People & Previous Episodes Mentioned: Episode 36: Community Over Competition (hustlehumblypodcast.com/36) Episode 129: How to Be a Good Co-Op Agent (hustlehumblypodcast.com/129) Hustle Humbly Community (hustlehumblypodcast.com/membership) Want to toast someone on the show? Send us a voice or video message with your name, who you are toasting, and why! Email it to team@hustlehumblypodcast.com. Leave us a review at http://ratethispodcast.com/hustlehumbly Get your FREE Database Template: http://hustlehumblypodcast.com/starthere Join Hustle Humbly Community! http://hustlehumblypodcast.com/membership Email Templates 101: http://emailtemplates101.com All Resources: http://hustlehumblypodcast.com Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

  6. Jun 22

    359: From Google Sheets to AI: Our Honest Real Estate Tech Stack

    Is your brain cluttered with every new tool, platform, and software someone told you that you absolutely need? Same. This episode started as a simple refresh of our tech stack after a listener wrote in asking what we actually use to run our businesses. Spoiler: the list is still shockingly short. But somewhere between Google Sheets and listing descriptions, we took a turn into AI territory, and y'all, we are not turning back. We walk through our bare-bones tech stack (yes, we still use a spreadsheet), talk honestly about how we are each using AI in our real estate businesses right now, and share why keeping things simple is not laziness, it is a strategy. We also get into SEO vs. AEO vs. GEO (yes, GEO is a real thing and it matters), what AI actually pulled up when Alissa searched herself, and the big announcement: Katy is teaching a monthly AI class inside the Hustle Humbly Community starting now. If you have been quietly panicking every time someone mentions AI, or if you have been using it already and want to go deeper, this episode is for you. Here's what we cover in this episode: The listener email that prompted this episode and our full simple tech stack answer Why simpler systems get used more consistently (and cost less money) Google Sheets, Trello, Canva, email, Google Drive, MLS, and yes, a little AI Transaction management and e-sign tools required by our brokerages How to qualify your tech choices based on the type of business you want to run SEO vs. AEO vs. GEO: what each one means and which one actually matters for your real estate business What happened when Alissa's seller looked her up with AI (hint: reviews matter a lot) How Alissa used ChatGPT to analyze multiple offers and review pre-approval letters Using AI to virtually stage photos, repaint rooms, and show sellers the vision How Katy used Claude to turn listing appointment notes and photos into a beautiful PDF checklist for a seller The Plaud device that listens to your appointments and summarizes them Why shiny tools do not fix broken habits Claude vs. ChatGPT: what is different and why Katy made the switch Projects, skills, and co-work inside Claude explained simply The new monthly AI class inside the Hustle Humbly Community for $25/month Why your Google reviews are your most important AI visibility tool right now Key Quotes & Takeaways: "Shiny objects feel productive, but they can delay real progress." Alissa "New tools do not fix broken habits. If you have systems in place that you're not using, a new system is not going to help you." Alissa "As long as you're running your business like a business and getting reviews from people, the internet and the AI are going to pick up on that." Alissa "You can not ask for more business if you are not taking care of the business you already have." Alissa "Using AI well will probably cut your task in half." Katy Products, People & Previous Episodes Mentioned: Episode 8: Tech Tools for Real Estate (hustlehumblypodcast.com/8) Google Sheets (free) Trello (free) Canva (free and paid) Google Drive (free and paid) ChatGPT (chatgpt.com) paid plan ~$20/month for photo editing Claude / Claude.ai (claude.ai) paid plan ~$22/month MLS e-sign (included with board dues) Dotloop (e-sign & transaction management) SkySlope (transaction management) Hustle Humbly Community (hustlehumblypodcast.com/membership) Email Templates 101 (emailtemplates101.com) Want to toast someone on the show? Send us a voice or video message with your name, who you are toasting, and why! Email it to team@hustlehumblypodcast.com. Leave us a review at http://ratethispodcast.com/hustlehumbly Get your FREE Database Template: http://hustlehumblypodcast.com/starthere Email Templates 101: http://emailtemplates101.com All Resources: http://hustlehumblypodcast.com Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

  7. Jun 15

    358: Who Actually Has to Sign? How to Protect Your Business

    Have you ever closed a deal only to find out you had the wrong person on the buyer rep agreement? Or listed a property without confirming who actually has legal authority to sell? This episode is your reminder that verifying identity in real estate transactions is not optional, and the stories in this one will make sure you never forget it. We are diving into a topic that sounds logistical but is actually one of the most important things you can do to protect your business: making sure you have the right signatures on the right documents from the very beginning. From buyer representation agreements to estate listings, from fraud prevention to identity verification, we are sharing real stories, real mistakes, and real solutions. Katy kicks things off with a wild story from a colleague whose buyers turned into a commission battle because a college daughter signed a buyer rep agreement with a Zillow agent while mom and dad were out of town. The result? A 50/50 commission split and a hard lesson learned. Alissa shares her own recent experience with a couple where the husband flat out refused to sign, plus the story of how a cash-paying dad showed up at closing and threw off her compliance paperwork entirely. We also get into estate sales, listing fraud on vacant land, power of attorney misconceptions, and why asking for a copy of someone's driver's license is never overstepping. Here's what we cover in this episode: - Why the buyer rep agreement is only as strong as the names on it - How to find out who will actually be on title before you start showing homes - What to do when only one party in a couple signs your buyer representation agreement - The procuring cause nightmare that the buyer rep agreement was supposed to fix - A first-hand story about a husband refusing to sign and how Alissa handled it - When a dad swoops in with cash at closing and suddenly you have the wrong buyer on paper - How to protect yourself when listing inherited or estate properties - Why you should ask for a copy of the will and contact the succession attorney before you list - What happens when a succession is not complete and your listing cannot legally sell - Vacant land fraud: the growing scam where someone pretends to be the seller - The truth about power of attorney and why you cannot do a POA for a POA - Why asking for a driver's license is not rude; it is just good business - How to use your broker as a buffer when clients push back on signing - Toasting Syed, a Realtor in Virginia who came to the US in 2022 as a US Army ally and grew from 2 transactions to 12 under contract for 2026 Key Quotes & Takeaways: - "The question isn't necessarily who's the buyer. Who do you see on the title? Who is going to be on the title?" Katy - "No one tosses up a fuss who is legit. If you say I need a copy of your driver's license and they say no, just push back. These are legal documents. I must verify your identity." Alissa - "If you cave at their first request, which goes against how you run your business, they are going to run the rest of the show." Katy - "This rep agreement is getting signed. It's the law." Alissa - "Clear, sincere communication matters more than perfect English." Syed (via Katy) Products, People & Previous Episodes Mentioned: - Episode 190: Wire Fraud and Real Estate Fraud with Nikki (title attorney) (hustlehumblypodcast.com/190) - Episode 317: Realtor Safety (hustlehumblypodcast.com/317) - Hustle Humbly Community (hustlehumblypodcast.com/membership) Want to toast someone on the show? Send us a voice or video message with your name, who you are toasting, and why! Email it to team@hustlehumblypodcast.com. Leave us a review at http://ratethispodcast.com/hustlehumbly Get your FREE Database Template: http://hustlehumblypodcast.com/starthere Email Templates 101: http://emailtemplates101.com Agent Systems 101: http://agentsystems101.com All Resources: http://hustlehumblypodcast.com Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com Music: Straight A's by Connor Price → https://connorprice.shop/ The Good Life by Summer Kennedy → https://soundcloud.com/summerkennedy/the-good-life Be The One by Matrika → https://uppbeat.io/t/matrika/be-the-one

  8. Jun 8

    357: Listing Struggles: Seller Prep, Photo Day, and Protecting Yourself

    Have you ever walked out of a listing appointment feeling like you just gave a masterclass... for free? In this episode we are talking about one of the trickiest catch-22s in real estate: you have to provide value to win the listing, but you also cannot give away the farm before anything is signed. This episode is a very honest, very practical chat about protecting yourself on listing appointments while still being the professional your sellers need. We started with a question from a listener who wanted to know how Alissa gets strict with sellers during the prep process without coming across as harsh or judgmental. The answer? It is less about being strict and more about knowing your job, explaining the why behind your advice, and having the confidence to deliver hard truths with warmth. We walk through real scenarios, including what to say when sellers push back on repairs, what happens when they show up to photo day without completing their checklist, and how to handle the overwhelming house that needs a phase two (and sometimes a phase three). Then we get into the part nobody talks about: how to actually protect yourself before you start spending hours helping sellers prep their home. We share what agents across the country are doing in their markets, including office exclusives, delayed listing options, commitment letters, and everything in between. And we remind you that if you are giving away all your best advice before anything is signed, that is a business problem, not a seller problem. Here's what we cover in this episode: Why the listing interview and the photo prep consultation are two completely different things (and why you need a hard line between them) How Alissa delivers the prep list with confidence and warmth, without sellers feeling judged What to say when sellers refuse to do the work: "We will need to adjust the price" The photo day story that taught Alissa to always do a pre-photo walkthrough Why phasing the prep process works (cookie jars first, deep clean second) How to frame staging prep as phase one of moving so sellers actually get it done The real cost of not prepping: price, days on market, and your own sanity How agents in different states (Georgia, Florida, Connecticut, Texas, Colorado, California, Oregon, Minnesota) are getting something signed before the consultation Office exclusive status: what it is, how it works, and why it protects you Commitment letters and listing agreements with future marketing dates What to do about reimbursable expenses if a seller cancels The builder story that reminded us sometimes you just have to stop marketing until they hold up their end Why your delivery gets better with experience, open houses, and being in the room Remember: price, location, condition. If condition is not right, price is the only lever left Key Quotes & Takeaways: "I do this to everybody. That's why I sell houses." - Alissa "Prepping for photos is phase one of moving." - Alissa "Listing interview and photo prep are not combined. There is a hard line." - Katy "If you gave them all that value and they had no problem throwing you to the curb, guess whose fault that is? Yours. This is really about running your business like a business." - Alissa "You are what you say you are. If you keep telling yourself you can't talk to people that way, you won't." - Alissa Products, People & Previous Episodes Mentioned: Staging Conversations Guide: hustlehumblypodcast.com/courses Hustle Humbly Community: hustlehumblypodcast.com/membership Want to toast someone on the show? Send us a voice or video message with your name, who you are toasting, and why! Email it to team@hustlehumblypodcast.com. Leave us a review at http://ratethispodcast.com/hustlehumbly Get your FREE Database Template: http://hustlehumblypodcast.com/starthere Email Templates 101: http://emailtemplates101.com All Resources: http://hustlehumblypodcast.com Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

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About

Join us for Hustle Humbly where we hope you will build the confidence to find your voice and your way to a successful real estate business and beyond. Listen in as Alissa & Katy, two top producing Realtors, talk about fostering community over competition while navigating the often times cutthroat real estate industry. With over 1000 homes sold between them and 13 and 19 years each in the business, they have seen it first hand. Deep dive into conversations and interviews about mindset and best practices with real life stories mixed in. The goal of Hustle Humbly is to reach out and encourage Realtors and business people alike to stop comparing themselves and start embracing their own strengths.

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