Buy Back Your Time: Mortgage Broker Jason Henneberry on Scale, Systems, and Entrepreneur Freedom

Jason (00:00)
The thing that matters most when you’re starting over is just get some revenue in the door. That’s it. And so no matter if I was starting over, the very first thing I would think of is how can I just make enough money to survive? That would be the first ring. And I would cut absolutely every expense in my life to get that nut down as small as possible.

Scott Bursey (01:58)
Hi everyone and welcome to the Real Estate Pros Podcast. I’m your host, Scott Bursey. And today I’m joined by someone I’ve really been looking forward to chatting with, Jason Henneberry, who’s been making serious moves in the FinTech and infrastructure space. And everybody, what happens when you mix a high level mortgage broker with a tech obsessed entrepreneur? You get today’s guest. From his early days in the industry to now leading Tango Financial and Nurture.

He’s seen every market cycle and built a solution for every hurdle. He’s one of the sharpest minds in the Pacific Northwest. Jason Henneberry is in the house. Jason, welcome to the show.

Jason (02:39)
Scott, that’s that’s

quite the intro. Appreciate it. Thanks for having me on the show.

Scott Bursey (02:44)
It’s our pleasure. I think our audience is really going to take something away from your master class on how to actually buy back people’s time. Jason, let’s dive in, shall we?

So first off for people who may not be familiar with your world, give us the short version. What’s been your main focus these days?

Jason (03:08)
Yeah, so my main business, I’m in the real estate finance space on the residential side and our core business. I have a partner of mine, Dean Larson, and we built and manage Tango. Tango is a national mortgage brokerage in Canada. We have about 600 mortgage agents across the country that we support.

Scott Bursey (03:28)
Awesome. And ⁓ if you can elaborate on the markets that you’re tackling right now, Jason.

Jason (03:36)
Yeah, so, you know, we’re primarily on the residential side for finance. We do have some people in our world that support commercial financing, but residential real estate financing has been our jam for quite a long time. And we’ve been doing this for just over 20 years or so. You know, started off as a solo entrepreneur, just being the mortgage broker and helping clients directly.

to building teams around us and ultimately, and it’s sort of one thing leads to another. The next thing you know, you’ve got a business that looks like Tango and we’re pretty proud of it.

Scott Bursey (04:16)
Love it. What caught my attention about you was the way you’ve been able to engineer the perfect pivot, if you will, from a high stakes mortgage broker to a tech driven visionary. know, Jason, that requires a level of surgical precision that most people just haven’t developed in this shifting economic climate. What’s been then unshakable pillar in your system that allows

your machine to scale without breaking even when the market gets volatile.

Jason (04:50)
That’s a good question, Scott. I think along the way you talk about surgical precision, it’s more like back against the wall, get scrappy, solve a real world problem, and if you’re lucky,

something comes of that. So I have a really good example of that. Back in 2016, we had some pretty major regulatory changes in our world that fundamentally changed how mortgage financing works in Canada.

And we had this moment in time where it used to be that everybody could kind of keep all the products and the rates in their head and just really focus on helping clients. And then that shifted out of nowhere. And so we found that we needed to build some tools to help make sense of just the growing complexity in the mortgage market so that our agents could help their clients get to solutions faster.

So we needed to do that. We just needed to do it for ourselves. The whole industry was having a bit of a moment. And what we ended up doing with that is we realized it made such an impact on our business that we decided to give it away for free. We gave it to the whole industry, this tool that we built. And within 30 days, we had about 1,000 users on the system and it just skyrocketed.

And it wasn’t perfect by any means, but we just put it out there. So we scratched our own itch and then we weren’t afraid to share it with others. And through that process, we got a lot of community feedback. It helped us build a lot of goodwill with the community. And then ultimately we ended up selling that piece of tech to a subsidiary of Rocket Mortgage actually. so that’s a really good example of, ⁓ you know,

Out of necessity came this beautiful idea and out of sharing with the community, we were able to actually turn it into a viable product that caught the attention of an entity like Rocket and we’re pretty proud of that.

Scott Bursey (07:41)
It’s a great example, Jason, of having your back against the wall and coming out like a champion. Hey, I tip my hat to you. That’s fantastic. Now, every operator I know has a moment where things got real. Maybe a deal, you know, went sideways or a time that you had to pivot fast. You mind sharing one of those moments with us?

Jason (07:53)
Thanks, man.

Sure, well, I mean that example that I just shared is one of them. I can think of another, I’m going a little bit further back in time. I had this marketing program when I was a solo operator. I had some team around me at the time, and this is going back about almost 15 years now, and we had basically a public seminar type approach for attracting clients back in 2006, 2007, and we brought in…

20,000 homeowners to our seminars over the course of a period of time and it was heavy on marketing because back then, you you couldn’t just fire up Facebook ads in the way that you can today or Google ads. So we were dropping flyers and doing radio ads and bus ads, all that kind of stuff. So very traditional marketing approach, very expensive way to get people to attend an info session and it was all in person. And we did that for a while and it worked pretty well but it…

but it started to not work as well. And so we had to make a big pivot and we pivoted from that into the online space back in 2011, 2012. ⁓ And so that was a major shift. There’s some, I’m giving you the 30,000 foot view on this, but there were some real painful moments in there where we realized that the money that we were spending on the traditional advertising wasn’t working anymore. We were digging a big hole for ourselves.

⁓ And this was post 2008 and there was you know for for for a couple of years we petered along because after 2008 The ⁓ stuff that we were talking about in our seminars. It just didn’t make sense to people anymore So we almost we got to the brink of bankruptcy and then we decided to pivot completely into online marketing and that felt scary at the time But it turned out it was a good idea and it actually created all the momentum that that that allowed us to do everything that we’re doing today

So was kind of a restart from scratch.

So don’t be afraid to reinvent yourself is kind of the message because what works in the past is it’s not guaranteed like that that’s going to work forever. And I think it’s important to just constantly keep things fresh so that you have some optionality. If something stops working that you maybe aren’t reliant on one particular business source, ⁓ there’s probably a lot of learning in there.

Scott Bursey (11:03)
a lot of learning and a lot of valuable substance. And Jason, that is just fabulous. That’s a couple of great examples of how you’ve taken a negative and rebounded strongly in the marketplace. Now that’s the real world grit that usually gets left on the cutting room floor. You know, most people want only the highlight reel version, right? But you’re giving us the actual blueprint for fighting, fighting deep in the trenches.

Going to war, if you will. And honestly, that’s the barrier to entry for the elite. It’s what separates the weekend, let’s say hobbyist, from the career operators who are still standing a decade from now. And that’s awesome. Let me ask you this, certainly. What are you most focused on solving or scaling next, Jason?

Jason (11:48)
appreciate that. Thanks.

I’m very interested in, I’m exploring this idea that an entrepreneur can build something new without negatively impacting what already exists. And so I have a few things in my world, I just shared a few examples, but I’ve been very fortunate in that our business, when we’re supporting all the people around us, it requires us to have

⁓ a little bit, ⁓ offer a little bit of support around business building, around marketing, maybe some coaching for helping the people in our space with business development, relationship building, all that kind of stuff. So as you do that, you realize that every once in a while you come across something that’s like, wow, this is really helpful and it could potentially help others, even outside of our little business, essentially. And so along the way we’ve created a few products that

⁓ have allowed us to expand our reach just beyond our existing network. So we tend to think in terms of like, what can we build or what can we do to support the people inside of Tango? And how can we do that in a way that ⁓ we don’t have to charge them or we can do it very cost effectively because they’re part of our group.

And usually these ideas require a heavy investment of time, energy, money, you you’re really thinking about things, you’re spending money on development. And so how do you offset that cost if you’re trying to deliver it for free? And the best way I’ve found to do that is to kind of productize what you’re doing and make it available externally for others in a way that, you know, people can plug into it. but they have to pay.

They’re not part of your group, obviously, you’re not gonna give it away for free for the rest of the world. That’s been a really good recipe for us in terms of it allows us to get larger market testing, but also brings awareness to what we’re doing and it acts as a lead funnel almost because people, they start seeing what you’re up to, they can plug in, you know, it’s very low consequence to sign up for a subscription for something and test the waters.

It allows you to build a relationship as an entrepreneur and then they realize there’s so much more available and it’s all free or it’s all included if they join your group, right? So ⁓ that model has worked really well and I’ve done that completely in the mortgage space. So my full reach is basically Canadian mortgage brokers and realtors and financial planners in Canada. I’m interested in exploring this concept. I’m on the precipice of…

testing this exact concept of can you build something that has broader reach, and I’m gonna try to build outside of my centers of influence, and can you do it in a way that every ounce of energy that you put into new project

also strengthens the old project, essentially. And so for the first time ever, I’m gonna test that theory. I’ve been able to successfully do it inside my niche.

Now I’m gonna try to do it outside my niche. And I’m hopeful that we’re successful at it, but also, you know, if we can share that journey that other entrepreneurs might be able to do something similar for themselves, because I think a lot of entrepreneurs are really good at their craft, and there’s probably a ton of things that they do really well operationally for themselves that they could leverage and share with others. And…

expand their reach and strengthen their existing business at the same time. And I think a lot of people, if you’re not entrepreneurial, that’s probably appealing to a lot of entrepreneurs.

Scott Bursey (16:31)
Well said and what great vision and along those lines of vision, what might be another vision that you have right now, a lofty goal or your next bullseye.

Jason (16:45)
All right, well, I’ll expand on what I just said. So I’ve written a book ⁓ and it’s a bit of a book about business. Some of the experiences that I’ve had building business, but I didn’t write it for the mortgage industry. I wrote it for entrepreneurs. And so my hope is that I’ll be able to share that concept, which, know, kind of like what we’re doing right now, and people will take interest. And through the sharing of that,

of that work, ⁓ I’ll be able to expand my reach. So that’s a big thing for me. I’m standing on the edge of, I haven’t reached out beyond my industry before. And so we’ll see if anybody likes it.

Scott Bursey (17:29)
I have a feeling that there’s going to be a lot of people that like it. And Jason, thank you for sharing that. I’ve got to ask you, if you were starting over today, let’s say with 50K and 10 years of experience, but you know, zero portfolio, what’s the first lead gen channel you’d turn on?

Jason (17:53)
Yeah, that is a great question. I actually have a start over story, like I did that. So if we go back to what I was sharing earlier about pivoting, I was about 10 years in the business. I had a well proven model. I basically blew myself up and I had to pivot. The most important thing, the thing that solves all problems, might have a grand vision, you might not know where you’re going, like you could be at either end of that spectrum. But the…

The thing that matters most when you’re starting over is just get some revenue in the door. That’s it. And so no matter if I was starting over, the very first thing I would think of is how can I just make enough money to survive? That would be the first ring. And I would cut absolutely every expense in my life to get that nut down as small as possible.

And that’s what I did. So back in 2010, 2011, my wife and cut, absolutely we cut, we canceled cable TV. We had three little kids at home. They’re all babies, like four, two and zero basically. And we cut out date night, we cut out coffee, we got down to eating beans. We streamlined everything. And we rented a tiny little house and we just like, we got down to the bare bones. And then we knew that we had so much runway with our savings.

and I started rebuilding from scratch, zero income. And we knew that we could survive for a year on our savings. And I just focused on how do I bring a dollar in to extend that timeline. That’s all I was trying to do, is how can we take this savings that we had that would allow us to survive for a year, and can I make half that money that I need and allow us to survive for two years, and then allow us to survive for three years. And what’s great about it is, ⁓

you know, if anybody’s like listening to this and they’re starting over and they’ve got a decade of experience, the one thing nobody can take away from you is like, is all of the experience you have, what you’ve learned and your capabilities. Because what I learned real fast is even though I had nothing and I was starting over, I was able to rebuild fast enough where I never had to touch my nest egg. I’d never touched it. I would, you know, it didn’t take long to get back to square one.

I didn’t have a business, I didn’t have a business plan. I just did the things that I knew how to do and reached out to my networks and I started that energy again. It wasn’t long before that turned into something. As you go, you realize you’re like, this is working and that’s working, and then you build from that. So ⁓ that would be my main focus. How you generate that business, I don’t know, but the focus would be on revenue, 100%.

Scott Bursey (20:42)
Certainly, and I knew there was more to the story. That is fascinating, truly remarkable really in its own right. And you know, that’s huge. That next move now, Jason, is where the leverage lives. It can either, you know, perfect your operations or detonate your workflow depending on the strategy that you deploy, I guess. Interested to know.

What would be your next object to overcome any hurdles that you may be facing, your challenges that you may be facing on the horizon?

Jason (21:21)
Yeah, for ⁓ myself in this moment, my next hurdle, or in that process of rebuilding the next hurdle, where are you going with that?

Scott Bursey (21:29)
It could be

either or, perhaps something that is next on the horizon here. A challenge that you may be facing, I guess, is what I’m trying to say.

Jason (21:41)
Yeah, okay, well, I mean, the biggest challenge that I’m facing right now is my desire to expand my reach beyond my current networks, to ⁓ try something, just step out on a limb, to try something new, writing a book. I have an idea of how down the line, I might be able to monetize that audience if I’m successful at building an audience, but the first thing I have to do is I have to build an audience.

But I’m also very aware that that takes a lot of effort. So I have to get the message out, it has to resonate, I have to refine that message. There’s a lot of work there. We gotta build the audience, we gotta nurture the audience. And I’m very conscious of the fact that I have my core business, the thing that drives all the revenue that gives me the freedom that I’m very fortunate to have to even consider spending time on this.

But so the biggest challenge is how do you put energy into that new thing without taking away from the existing thing? And better than that, it’s like how can the energy that you invest in new project actually strengthen existing project? And so I’m very much trying to figure out that recipe. yeah, I’m pretty sure we’re gonna be able to do it, but there’s some work that still needs to.

be done there to think that through properly.

Scott Bursey (23:10)
I have confidence in you and your abilities to sift through that. And thank you for sharing that with us. At this level of the game, proximity, you know, is power. The math of the deal only gets you so far, I guess. It’s the depth of your connections that determines who actually gets to the closing table. All right, before we wrap, if someone wanted to reach out, connect with you, maybe collaborate or learn more about what you’re up to.

What’s the best way for them to reach you?

Jason (23:41)
Sure, yeah.

There’s probably two ways. I’m pretty accessible. So my handle on pretty much any social media platform is @JasonHenneberry. I’m sure there’s some show notes. We can put a link there. And then if you’re curious about checking out the book, it’s called Dependency Design and it’s at dependencydesign.com and it talks about why founders are

We often end up building a business that should create freedom for ourselves and give us options, but often ends up feeling heavier than we expected. And we, you know, we try to explore that concept for entrepreneurs. It’s a short read. It’s like 15 minutes. It’s more of a PDF than a book, Scott, honestly.

Scott Bursey (24:28)
Perfect. Thank you for that. And I appreciate your time, your story, and your perspective. And I have found that the people that contribute the most to the world are the easiest to speak with. And you’re no exception. Thank you. Thank you for your time.

Jason (24:43)
Appreciate that. Thanks, Scott. Thanks for having me on the show.

Scott Bursey (24:47)
We need more people in the space that are doing it the right way. And for those of you tuning in, if you got value from this, make sure you’re subscribed. We’ve got more conversations coming up with operators just like Jason, who are out there building real businesses. We’ll see you in the next episode, everybody.