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Stephen Whiting is Co-founder of StreetText, an ad tech platform that integrates with Meta to provide businesses with agency-level ad capabilities in-house. Since its inception in 2012, StreetText has transformed real estate marketing, helping clients generate over 5 million leads and achieve hundreds of millions of dollars in value. As an experienced real estate agent, Stephen gives real estate professionals and various other industries the tools to generate leads and effectively run ad campaigns.

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Here’s a glimpse of what you’ll learn:

  • [3:25] How StreetText leverages data to create effective ad campaigns easily deployable in just a few clicks
  • [4:31] The personal backstory of Stephen Whiting and the pivotal moments leading to StreetText’s inception
  • [5:09] Why StreetText initially targeted real estate before expanding to other industries
  • [12:35] The success of converting traditional real estate advertising into a digital format
  • [16:00] The transition from a tech-enabled agency model to a fully self-service SaaS platform
  • [22:23] Insight into StreetText’s pricing strategy and its evolution over time
  • [26:09] Core features of StreetText: sophisticated ad management and remarketing capabilities
  • [28:18] How StreetText’s one-click split testing feature evolved to lower ad costs by targeting the right audience
  • [33:52] The value of remarketing back to your existing audience
  • [41:39] The value of growth through partnerships

In this episode…

Have you ever wondered how minute tweaks in your advertising approach could dramatically shift your business’s success? Imagine spending your last few dollars on an ad campaign only to find the answer that creates a surge in leads. Can a single moment of strategic insight change the game for entrepreneurs?

Marketing expert Stephen Whiting discusses how a desperate bet on a Facebook ad led to the establishment of a platform that revolutionizes the way real estate professionals — and now individuals from various industries — generate and nurture leads. He shares the journey of StreetText from its humble beginnings with text-based sign riders to the development of their full-fledged ad tech platform that simplifies and enhances digital advertising. Stephen divulges how they navigated the shift from functioning like an agency to becoming a scalable SaaS business and how pricing strategies played a key role in their growth.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Stephen Whiting, Co-founder of StreetText, about building an innovative ad tech platform for real estate. Stephen discusses the significance of understanding your audience, the importance of constant testing in advertising, why content must be put in front of potential leads to avoid being lost in the digital abyss, and how partnerships have been a valuable growth asset for StreetText.

Resources mentioned in this episode:

Special Mention(s):

Related episode(s):

Quotable Moments:

  • “Top of the funnel is the best way to go.”
  • “If you can capture data around things that are working and provide those insights to other clients, they will be much more successful when they run ads.” 
  • “Creating content is a must — but on platforms like Instagram and Facebook, it goes to die. So what we do is we take that best-performing content — and it lives on forever.”

Action Steps:

  • Take advantage of ad tech platforms to simplify and streamline your digital advertising efforts.
  • Using specialized software like StreetText can help businesses avoid the confusion of complex ad managers and focus on strategy.
  • Utilize proven marketing templates to jumpstart your campaigns.
  • Leveraging successful templates and case studies can save time and resources in ad creation and testing.
  • Conduct split testing on your audience to refine your ad targeting.
  • Testing different audiences with the same ad can lead to more cost-effective and efficient lead generation.
  • Implement continuous remarketing strategies to keep your brand top-of-mind.
  • Regularly engaging potential leads with remarketing can lead to long-term sales and customer retention.
  • Embrace partnerships and collaborations for business growth.
  • Forming strategic alliances with influential partners can accelerate the reach and implementation of your products and services.

Sponsor for this episode

At Rise25, we’re committed to helping you connect with your Dream 100 referral partners, clients, and strategic partners through our done-for-you podcast solution.

We’re a professional podcast production agency that makes creating a podcast effortless. Since 2009, our proven system has helped thousands of B2B businesses build strong relationships with referral partners, clients, and audiences without doing the hard work.

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The Rise25 podcasting solution is designed to help you build a profitable podcast. This requires a specific strategy, and we’ve got that down pat. We focus on making sure you have a direct path to ROI, which is the most important component. Plus, our podcast production company takes any heavy lifting of production and distribution off your plate.

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We’ll distribute each episode across more than 11 unique channels, including iTunes, Spotify, and Google Podcasts. We’ll also create copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90xAtariEinstein BagelsMattelRx BarsYPOEOLending TreeFreshdesk, and many more.

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.

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Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

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Episode Transcript

Intro 0:15 

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Jeremy Weisz 0:22 

Dr. Jeremy Weisz here, founder of I talk with inspirational entrepreneurs and leaders today is no different. I’ve Stephen Whiting of, before I inch formally introduce you, Stephen, I always like to point out other episodes, people should check out the podcast, and this is this is gonna relate to paid ads, and sometimes even the agency worlds it’s kind of like a cross between SaaS and agency. But I have Jason Swenk on the podcast, who talked about how he built up an agency to eight figures and sold it and then he’s been buying up agencies, he also has an agency group. That was a really interesting interview.

Also talk to Kevin Hourigan. Kevin has had an agency since 1995. So he’s really talked about the evolution of the space and his services and the companies. That was an interesting one as well check more of them out on And this episode is brought to you by Rise25. At Rise25 we help businesses give to and connect to their dream 100 relationships. And how do we do that we actually do that by helping you run your podcast, we’re an easy button for a company to launch and run a podcast we do the strategy, the accountability and the flex acumen and Stephen, we call ourselves the magic elves that work in the background and make it look easy for the hosts so they can build amazing relationships, create great content and just run their business.

For me, the number one thing in my life is relationships. I’m always looking for ways to give to my best relationships. And I found no better way over the past decade to profile the people in companies I most admire and share with the world what they’re working on. So you’ve thought about podcasting, you should if you have questions, go to to learn more. And I’m excited to introduce Stephen Whiting. He’s the Co-CEO of StreetText and StreetText is an ad tech platform. Integrated with metta giving businesses agency-level ad capabilities in-house and Stephen, I think I believe people can log in to StreetText, and actually run their ads from StreetText, and not go into.

I mean, I don’t know, for me, it’s complicated going into the Facebook ad manager and I’ve only this is not my expertise at all. But I could see how much easier better interface would make it so much better and easier. And Stephen’s worked with meta since the day it opened up ads in the newsfeed in 2012. And StreetText has worked extensively in the real estate industry. And their customers have generated over 5 million leads, translating into hundreds of millions of dollars in value. And StreetText serves other industries and agencies alongside the real estate niche as well. So Steven, thanks for joining me.

Stephen Whiting 3:08 

Thank you, I’m very excited to be here.

Jeremy Weisz 3:10 

It’s really cool, what you’ve created here. Just talk about StreetText and what you do. And if you’re listening to audio, there is a video piece and I’m gonna poke around StreetText as Stephen talks. So tell us a little bit more.

Stephen Whiting 3:25 

Perfect. Thanks. Thanks, Jeremy. So StreetText is an ad tech platform, like Jeremy said, that’s connected to meta. So we make it very, very easy to run ads, effective ads and do them well. So if you’re looking to meet new clients or grow your business, but you really don’t like the ads manager, because you find it confusing, it’s always changing. Well, you’re not even really sure what to look at or what to checkout, or where a lot of people get stuck, what do I even run, when you come into our system, we actually aggregate all of the data that’s running through our platform.

So you get to see exactly which ads are performing, how they’re performing, you get to see all of that data behind the scenes. So if you’re gonna go run an ad, you don’t have to figure it all out, spend a whole bunch of money testing creative and copy and messages, our system actually has a lot of that figured out for you. And we make it easy to deploy ads and just like literally one to three clicks and you have an ad running. There’s a whole bunch of other tools behind the scenes as well, including a ton of remarketing. We have ways of optimizing the audience. We can even rotate ads, there’s a lot in there. But in a nutshell, that’s what we do. And, we make it really easy.

Jeremy Weisz 4:31 

Yeah, we’ll talk about what you consider a secret weapon and also split testing and other things. But I’m curious about the niche early on because you serve a lot of real estate. I’m curious, early on. To me, it seems like a very cool tool for agencies to use to run things for their clients. So yeah, I’m just interested on how you kind of got into this. You went all in on the real estate niche, and I know you help other niches. But why that as opposed to maybe going after agencies using the platform.

Stephen Whiting 5:09 

So, many, many years ago, like this is a long time ago, even before the financial crisis or kind of during — I was a real estate agent myself. And I had some background on like real estate development, and they got into commercial and residential. And so I enjoyed it, I really love doing what I did, but we just couldn’t help ourselves in creating a software product. And it took a few iterations to lead to where we are today. The name StreetText actually comes from these text double signwriters, where people can text a number, I don’t really remember this. So maybe some of your listeners were aware, you could have a, like a sign on top of the for sale sign, and it would say, like text this number to this number, and you’ll get all the information about the property on your phone.

And that was a long time ago, but we were basically the first in Canada to run that initially. And that’s where the name came from. And then a few pivots later, we landed on what we do today. And that’s when it really obviously took off for us. And but yeah, so anyways, all that to say, we would have all these real estate agents, so obviously creating StreetText, we went after real estate agents with a taxable sign writers, then I had all these agents and I couldn’t really scale that business, it was a nice to have, but not really a must have. And but I had all these agents saying, I love the fact that we’re generating leads from the signs, is there any way you can generate more of those. And that’s when Facebook at that time, not Meta. But when Facebook opened up the newsfeed, and you can start to run ads, before that a lot of the ads were running kind of, back in the early days of Facebook, kind of all over the screen, and they didn’t really have a lot of ROI. And Facebook knew that.

And then they started opening up in the timeline in the newsfeed. And that’s when they started to really gain traction, because I think for people that were observing or like scrolling the newsfeed, it became harder to tell the difference between a post and an ad. And that proved out to be very successful. And so anyways, we jumped on at that particular point of time, I can tell you some crazy stories if you want and how we actually landed on a very first customer, because we were done. I mean, it was down to the last few $100 A client gave us I can get into that story if you like. And anyways, we found it. And then once from that point on, we were able to scale and then because we were working with real estate agents that sort of naturally spread and we’ve dabbled in other businesses along the way, but stayed fairly close to the industry. But now we’re a lot broader. We’ve opened it up.

Jeremy Weisz 7:38 

So yeah, definitely talk about the last few $100. But again, before you get there, I’m curious. So the first version was someone would text the sign? And would your software automatically send that information to people when they text it?

Stephen Whiting 7:57 

Exactly, yeah. So we would send the information to the consumer. And we would collect the information, obviously, from the consumer, we would give that to the real estate agent. And that was before apps. That was really when people were still relying a lot on text messaging to get information. We even had these, you can have a smartphone or a dumb phone, and that was because some phones only had text capability back then, a lot has changed obviously since then. But those are the early days. And but yeah, I was working with this. We’re working with a number of real estate agents, but we were selling a $ 15-a-month product. Plus, we would have to phone the agent and explain to them how this whole thing worked. And so it wasn’t scalable. I mean, you could not get a sales team or a team around explaining how everything works and selling it for $15 a month. It just didn’t work.

Jeremy Weisz 8:46 

But to them, you’re like we just were unprofitable.

Stephen Whiting 8:50 

Yeah, but when you’re young and you’re getting started, you know, that’s part of the journey is because you just think to yourself, oh man, if I can get like 1,000 or 10,000 agents, this is gonna go great. You know, and so anyways, we were doing that, and it’s working, but not scaling. Back then my brother John and I, we had another partner in the business too. But I mean, we were paying ourselves. If we could $1,000 a month, we’re trying to pay some staff, it was really tough going back then all the money was going back into the business. But you’re just an entrepreneur and you’re believing in what you’re doing.

And we were working with this client, Darrell Ruder, who was actually, I’d known him for many years, but he basically was one of the clients that said to me, “Look, if you can generate leads for me outside of this on Facebook, I’ll give you $500.” And I was not an advertiser, like, at that time, I’d never run ads. And so I did everything I could to learn in 2012 and 2013 and getting in 2014, over those kind of early years of the newsfeed but I took that $500. I was trying a bunch of different things.

And I’d also bought a house that I was renovating and my first daughter was about to be born. And the company was just like nose-diving. And it was a really stressful time. And I remember, I was down to probably the last 50 or $60, I had generated him like nothing. This is one of the things about ads that show crazy, you can have an ad that looks very similar to another ad. But if the copy is wrong, or something’s just wrong, Facebook will take your money on it, and they’ll spend it, but you’ll get nothing out of it. And if you got the ingredients, right, and I guess the formula, right, if you will, all of a sudden you can generate leads. And so I went to a Starbucks in the morning, it was a Sunday, I ran this last ad, I literally had about $50 left of this advertising money, I launched an ad that I thought was going to work, I went home, and I was now lifting up this glue laminate on my kitchen floor. And some of the worst work you can imagine.

Because you’re trying to break this laminate up and it’s glued down. So it’s coming up piece by piece. And my phone just kept buzzing, I thought somebody was trying to call me over and over. But I was so frustrated with a lot of things at that time. And this particular floor that I just didn’t want to move away from it. And so I’m lifting up the floor, and it just kept buzzing. And eventually I will go over to my phone to see who’s calling me. And I had set up to show me like a new lead. And it just said new lead, new lead, new lead, I probably had 35 of them. And I just knew in that moment that we had cracked it. And from that point on, that’s really where StreetText took off.

And again, it was a small change. And so what we did is we took even that existing ad. And we began to realize early on that if you can capture data around things that are working, and then you can provide those insights to other clients, they will be much more successful when they run ads, because they will now launch a proven template that will work and they can iterate from that. But they will be very frustrated like I was if they start from nothing. And that’s really was the essence of StreetText started and began to grow.

Jeremy Weisz 12:06 

What was in that template that you had struck because you tried other things?

Stephen Whiting 12:11 

Yeah, it’s funny, what’s old is new again, right? Like, so what I, we were running at that particular time, a home Valley ad, which was very similar to and I’m sure you’ve all seen them, you know those real estate agents will send you, what’s my home worth probably in the mail, and gets the some of that information. So I took a few of those. And I basically created a digital version of them.

Jeremy Weisz 12:35 

You’re like working in the mail, and they’re mailing out with stamps, maybe it works online.

Stephen Whiting 12:41 

It’s funny because all the things that you thought would be more kind of, I guess, modern, or digital or sexy, if you will, they just weren’t landing. And I took this and I used some of the copy that seemed to be working for an agent that kept writing it. And I modified it for the purpose of the ads, and it worked. And then from that point on that particular ad for us, still is alive and well today, the exact same copy from over a decade ago still works. And we’ve had a lot of real estate agents that have come in over the years. I mean, we’ve worked with so many of them. And some of them have come in and said, oh, that’ll never work. And so we have all the data on it. So you can actually see the data, they get to see the data on it. So they kind of hum and haw, then they launch it. And they’re shocked how well it can work. And so again, coming back to that proven template if you can get those that, you know, a starting spot, an initial spot, and you can again, iterate from there. But I’d say a lot of businesses, just give them what works. And they’re happy with that.

Jeremy Weisz 13:44 

Why do you think they thought it wouldn’t work?

Stephen Whiting 13:48 

Well, I think we make a lot of decisions based on what we feel like we would do. Right, and I’m just as guilty. I mean, I look at some of the marketing that I’ve seen, even other marketers do, and I go I don’t like that. I don’t think that’ll work. Right. But it does, right? And then you see that business grow up or explode or they’re scaling like crazy. And you go, you know, maybe there’s something to that. And so yeah, I think those are just the biases we all carry.

Jeremy Weisz 14:15 

I’m curious in the beginning with the text piece, were you capturing the data and putting it in a database? And that or for the original version? Is that what was happening?

Stephen Whiting 14:31 

Yes, yeah. So the StreetText back then that you would log into looked very different I mean, it was all about the signs that were connected to properties. And we would then capture this lead and show you which property it came in on. And then you know, give you an email notification as well.

Jeremy Weisz 14:52 

It’s interesting, because at that time, that’s pretty sophisticated. And you could have gone a totally different route even because like I had the founder of T-Tango on that sends text messages or you know, like that actually is a database for text. Do you mean you could have gone that route, too? But you went to the Facebook ad.

Stephen Whiting 15:13 

Here’s another big one, too. I mean, we even toyed back then I mean, we wouldn’t have been able to execute like they did. But this is before Twilio. And so we used to spend a lot of time thinking, could we take this technology and create more of a platform that other businesses can work on? And now Twilio executed on an incredibly well, I mean, they’re public now? Yeah, they absolutely are. And they’re done very well. But, but the point was, there was a lot of other use cases to your point. And that’s what I love about business, too, is that you kind of get into it, and then you get a little bit more insight, and then you make another decision to get more insight. And you just kind of continue on.

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