March 19, 2026
Value Pricing Role Play: Real Estate Startup Edition
One of the Ditchers down in Ditcherville asked a question this week about how to use value pricing for a potential client starting a new business.
It went something like:
How do you run the Why Conversation for startups / MVPs where the business doesn’t exist yet?
Classic question.
I’ve always wanted to come up with a way to role-play The Why Conversation in situations like this, but I’ve never had much luck.
Since I have an AI assistant now, I thought maybe that would do the trick, so I gave it a try, and the results were surprisingly good!
Following is the exact text of my AI roleplay. I didn’t do a full Why Conversation, but the dialog gives a good example of drilling down to get at the core value of the minimum viable project.
Here it is:
———
Founder:
Hey Jonathan, thanks for taking the call. So I’ve got this idea for a SaaS platform — basically, it’s an AI-powered scheduling tool for real estate agents. I’ve mapped out the whole thing. I need a booking engine, CRM integration, automated follow-ups, a mobile app, and a client portal. Can you give me a ballpark on what something like this would cost to build?
Jonathan:
Yes, I definitely can give you some prices once I’m sure of what we’re trying to achieve. Would it be okay to ask you some questions?
Founder:
Yeah, of course. Fire away.
Jonathan:
How did you decide on the list of features that you just described to me?
Founder:
Well, I’ve been a real estate agent for twelve years, so I know the pain points. I talked to a bunch of other agents in my office, and they all have the same problems with scheduling and follow-up. And then I spent a couple of weeks with ChatGPT mapping out what the product should look like. It gave me a pretty solid feature list.
Jonathan:
What are the top three pain points they shared with you?
Founder:
OK so the biggest one is double-booking — agents are constantly scheduling showings that overlap because they’re juggling everything in their heads or on paper. Second is follow-up — after a showing, most agents just forget to follow up with the buyer and lose the deal. And third is just the back-and-forth with clients trying to find a time that works. It’s like endless texting.
Jonathan:
Let’s focus on the top one, which you say is double booking. How big of a deal is this, from a financial perspective?
Founder:
Hmm, I mean, it’s definitely embarrassing when it happens, but financially... I guess if you double-book and have to cancel on a buyer, sometimes they just go with another agent. So you could lose a commission. A typical commission on a sale around here is maybe $8,000 to $15,000. I’d say it probably happens to most agents a few times a year. But honestly, I haven’t really put a number on it.
Jonathan:
So if I understand you correctly, real estate agents are suffering from double bookings roughly three times a year and losing on average about, let’s call it $10,000? If so, this would net out to $30,000 of lost income per year? Is that fair, or is that an overstatement?
Founder:
No, I think that’s probably right, actually. Maybe even an understatement because there are also times where you don’t lose the client, but you damage the relationship, and they don’t refer you to their friends. But yeah, $30K feels like a reasonable floor.
Jonathan:
Based on your conversations with your real estate agent friends, how much do you think they would gladly pay to recoup this $30,000 of lost income annually? Would $3,000 seem reasonable?
Founder:
Oh easily. Three grand to save thirty? That’s a no-brainer. I think most agents would pay even more than that, honestly.
Jonathan:
How much do you think they would pay to solve this double booking problem?
Founder:
I mean... probably up to five or six thousand a year? Maybe more for the top producers. If you’re a high-volume agent doing forty to fifty transactions a year, double-booking could cost you way more than $30K. So maybe even ten grand wouldn’t be unreasonable for those guys.
Jonathan:
Okay, so let’s say we focus specifically on this double booking problem and assume that real estate agents would happily pay $6,000 per year to solve it. What’s that, $500 a month?
Founder:
Yeah, $500 a month. That feels right for the high-end agents. Maybe you’d need a lower tier for the smaller agents, but yeah, I could see that working.
Jonathan:
Let’s focus on the high-end agents paying $500 a month to solve the double booking problem. How big is the market for these high-end agents? How many of them are there?
Founder:
In my metro area, there’s probably about 200 top producers. Nationally? I mean, there’s gotta be tens of thousands. But realistically, I’d be starting local. If I could get even 50 of the 200 in my area, that’s $25,000 a month in MRR right out of the gate.
Jonathan:
So getting 25% of the local market share as a starting point would be a big win for you?
Founder:
Huge win. That would be $300K a year in recurring revenue. That’s more than I make as an agent. If I hit that number, I’d probably go full-time on the product.
Jonathan:
All right, I’m convinced that the double booking problem is an expensive problem that’s worth solving. If we just focused on solving this single problem, how would you revise your original idea about what the MVP would require?
Founder:
Wow, yeah. I mean... if we’re just solving double-booking, I probably don’t need the CRM integration, the client portal, or the automated follow-ups. At least not right away. It’s really just the booking engine and maybe some kind of calendar sync so it can see what’s already scheduled. That’s way simpler than what I came in with.
Jonathan:
You’ve got over a decade of experience as a real estate professional. What do you personally think is the biggest cause of double bookings?
Founder:
Honestly? It’s that most agents are managing their schedule in three different places. They’ve got their personal Google calendar, then whatever the brokerage uses, and then half the time they’re just confirming showings over text and forgetting to put it anywhere. Nothing talks to each other.
Jonathan:
So it’s their calendar, their texts, and then some system their brokerage uses? What’s the biggest brokerage management system in your area? I assume there’s one big one and maybe two much smaller ones.
Founder:
Yeah, most of the big offices around here use BrokerMint. There’s a couple on Dotloop and a few using SkySlope, but BrokerMint is probably 60-70% of the market locally.
Jonathan:
And how many of the brokers are using Google Calendar versus something else?
Founder:
Almost all of them use Google Calendar personally. A few of the older agents are still on Apple Calendar, but it’s overwhelmingly Google. I’d say 80% or more.
Jonathan:
And what are they using for text messages with clients?
Founder:
Just regular texting. iMessage, SMS. A few of the more tech-savvy ones use something like Heymarket or Grasshopper so they can keep a separate business number, but most agents are just texting from their personal phone.
Jonathan:
How many of them are using iPhone versus Android?
Founder:
Almost all iPhone. I’d say 90% easily. Real estate agents are big on iPhone.
Jonathan:
Okay, so if we were going to initially solve for brokers using Google Calendar, iMessage on iPhone, and BrokerMint, how many real estate brokers in your local area would that account for?
Founder:
Out of those 200 top producers? Probably 150, maybe even more. That’s a huge chunk of the market. I hadn’t thought about narrowing it down that way, but yeah, that covers almost everyone.
Jonathan:
If we had a kick-ass solution with a 100% money-back guarantee, how many of those 150 do you think you could convince to participate in a beta test?
Founder:
I mean, with a money-back guarantee and me personally knowing most of these people? I bet I could get 20 or 30 to try it. Maybe more if I pitched it at one of the monthly broker meetings.
Jonathan:
So if those 20 or 30 turned into paying customers after 3 months, what would your MRR look like at $500 a month?
Founder:
That’s $10,000 to $15,000 a month. So $120K to $180K a year in recurring revenue just from the beta group. That’s... actually really compelling.
Jonathan:
Assuming you got glowing testimonials from those 20 or 30 people, how many more do you think you could land in your local area alone in the next 9 months?
Founder:
With real testimonials from agents they actually know? I think I could get to 80 or 100 pretty easily. Word of mouth is everything in real estate. If three or four top producers are raving about it, the rest are going to want in.
Jonathan:
So run the numbers — what would that look like for your MRR?
Founder:
That’s $40,000 to $50,000 a month. So roughly half a million a year in recurring revenue. Just from my local market. And that’s before going to other cities.
Jonathan:
So if I can put something together that made this a reality for somewhere between $250,000 at the high end and $50,000 at the low end, would that be worth considering?
Founder:
I mean, yeah. If we’re talking about something that could generate half a million a year, spending $50K to $250K to get there is a pretty obvious yes. Even at the high end that pays for itself in six months.
Jonathan:
And you’re fine leaving out all of the other features from your original MVP vision and focusing specifically on this group as a starting point?
Founder:
Honestly? Yeah. Coming into this call, I thought I needed all five features to launch. But just solving the double-booking problem for top producers in my area is way more focused and way more realistic. I can add the other items later once we have traction.
Jonathan:
Agreed. And you’d have enough cash flow to experiment with growing the market either vertically or horizontally. I can have a proposal to you by Wednesday, 3 days from now. Is that acceptable?
Founder:
Absolutely. I’m excited. This feels way more doable than what I had in my head when I called you.
Now...
If I were really doing a full version of The Why Conversation, I’d also have asked “Why Now?” and “Why Me?” questions to help me close the deal after having uncovered the value.
But hopefully, you found this synthetic conversation useful.
If not, PLMK.
Yours,
—J