593 Jason Henneberry

[00:00:00]

Founder Dependency Myth

Jeffrey Feldberg: Most founders believe that if they hire the right people, build better systems, and learn to delegate, eventually the business will stop depending on them.

Jason Henneberry believes that very assumption may be the problem. Jason is the founder of Dependency Design, the author of Why Your Business Won't Let You Go, and a senior leader at Tango Financial, a national mortgage organization supporting more than six hundred professionals. His career has included building companies, developing technology, selling a technology product to Rocket Mortgage, earning multiple mortgage industry awards, and discovering firsthand how success can quietly turn the founder into the biggest dependency inside the company.

But Jason's story also includes the other side of entrepreneurship. In two thousand and eight, after making a massive bet just as the market collapsed, [00:01:00] he came frighteningly close to losing everything. He rebuilt, started again, and eventually helped scale a mortgage platform handling billions of dollars in annual volume.

Those experiences led him to a fascinating conclusion. Handing someone a task is not the same as handing them ownership. And sometimes the very instincts that make a founder successful, stepping in, solving problems, protecting the company, can be the invisible architecture keeping that founder trapped.

Jason's work asks a deceptively uncomfortable question: Did your business become dependent on you because it needed to or because you accidentally trained it to?

And before we start this episode, a quick word from our sponsor, Deep Wealth and the 90 Day Deep Wealth Mastery Program. Here's Jane, a graduate who says, and I quote, the Deep Wealth Mastery Program prevented me from making what would have been one of the biggest mistakes of my career. [00:02:00] I almost signed on the dotted line with an unsolicited offer that I now realized would have shortchanged my hard work and my future had I accepted that offer. Deep Wealth Mastery has tilted the playing field to my advantage.

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So what do you think?

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Meet Jason Henneberry

Jeffrey Feldberg: Deep Wealth Nation, welcome to another episode of the Deep Wealth Podcast. Deep Wealth Nation, you heard the official introduction. We have a fellow founder, not just a founder, someone who's done multiple startups, multiple exits, a fellow post-exit entrepreneur, an author. You name it, he's done it. He's been there.

I have a real treat for you today, but I'm gonna put a plug in it right there. My goodness, Jason, firstly, welcome to the Deep Wealth Podcast. There's always a story behind the story. Wow, you have quite the story. So what's your story? What got you from where you were to where you are today?

Jason Henneberry: Jeffrey, thanks for the nice intro, and thanks for having me on the show. All those accolades come with a few bumps and bruises along the way too. I've been pushed around and beat up a little bit, but we're here to tell the tale, so y- that's a good thing.

From Broker to Platform

Jason Henneberry: I could give you a little bit of context for what I've done over the course of my career, just 30,000 foot. Might be [00:06:00] helpful to just start where I am today. So I've got two businesses that I run currently. One is very much in startup mode on the marketing support side, and it's an ancillary business to my main business.

We're trying to get that off the ground. and then the main business is pretty mature. We're in the mortgage finance space. We have a company called Tango Financial, and we basically do back office admin support for mortgage agents and mortgage brokerages across the country. So we have about 600 agents in the network from coast to coast.

I'm on both ends of the spectrum, mature business and startup. I started like most entrepreneurs, though. Like you know, I started off as a solo mortgage broker, just trying to get out there, build referral relationships, and develop some business for myself, and this is going back about 25 years now.

And you plug away. One thing leads to the next, and before you know it, if you're lucky, you've got a little bit of success, and you start building some systems around yourself to be more efficient. Maybe you hire someone. I like to joke around that I've had 12 first assistants [00:07:00] because it takes forever.

If you don't have a sense of how to hire someone the first few times you do it, it's, it can be rocky. Lots of lessons learned there. But eventually, you figure that out, and we were able to build some cool systems and have some really great people around us, and that led us to building Tango eventually, which basically, we leveraged all the things that we were doing for ourselves, scratching our own itch in our business, and then we realized that, if we have these problems, then maybe the rest of the industry has the, these problems, and we started to make our platform available to others, and turns out that was a pretty good idea.

And I think a lot of entrepreneurs do that. You do your own thing, and if you do it really well, suddenly you have value that you can offer the broader market, 

Jeffrey Feldberg: absolutely. And by the way, Deep Wealth Nation, please go to the show notes, all the links, all the resources, information's gonna be there. But in there will be the link to Jason's site, and the price is right. Get the e-books that are there, because I gotta tell you, Jason, when I was preparing for today, for book number one, Why Your [00:08:00] Business Won't Let You Go, it had Jeffrey written all over it. In fact, it

still has Jeffrey written all over it e- even today with what I've done, and I was laughing and chuckling, and I was right there with you in terms of what's happening with the founder dependency. And in fact, you'll get a chuckle out of this one. Someone joins our 90-Day Master program, one of the first questions we ask, "Does your business run without you?"

It's a yes or no. stories, no in-betweens. I don't care if you have a leadership team or a management team, I rarely hear the yes or no. I hear a no, but, or a yes, but, or let me tell you this,

Jason Henneberry: Yeah.

Jeffrey Feldberg: the map. So right there with you. tell me, I'm gonna be all over the map. There is a method to the madness. 

Building a Marketing Assistant

Jeffrey Feldberg: On the marketing side that you quickly skip past at the very beginning, what's going on there? Because just about every founder I speak with, this is a pain spot for them. And you've been successful. Wow, 600 agents and counting on the established business with Tango. No easy feat. You've been around [00:09:00] the block a few times, lots of lessons learned. Where we are today, artificial intelligence or now super intelligence and social media and people wanting more and more and more. So where are you on that side in terms of marketing?

Jason Henneberry: I'll tell you. everything that I've been able to do in my career has been in and around the Canadian mortgage industry, a very small market, business to business. So we have about 15,000 participants coast to coast, and I've been able to build multiple businesses and have some exits and do some pretty cool things.

What I have not done is I have not built a personal brand outside of the mortgage industry. Because I've built some cool tools and I've made it available to the whole industry, I have good brand presence inside my own industry. But I see the power of having a broader audience. And I'll tell you a quick story.

My, son, who's 20, he's been plugging away at social media for the last couple of years, and I'm watching him do his thing, and he is now past two billion views across his channels half a million-plus subs on his direct channels, and he's got a bunch [00:10:00] of other faceless stuff. the power of that, that audience what he's able to do with that is just, it's mind-blowing to me.

And so I've realized in the last couple years that I could benefit from doing more of that, or I'm, at least curious about what it's like to do that. And so I'm a busy entrepreneur. I don't have a lot of time in the day, I've tried a couple of rounds at launching a social presence and doing the marketing and doing all the things you're supposed to do, but it really is a bit of a grind.

And I haven't been able to find the right tools to do it. And I've tried hiring marketing managers to support me. But at the end of the day, the workload still landed on me for coming up with the y- all of the brand decisions and doing a lot of the work, and it still took hours.

So I am trying to solve my own itch again by streamlining that process. I wanna be able to wake up and say, "You know what? I have a thought. I wanna write an article about this concept, and then I want a script, and I want an email, and I want a social media post, and I want it to go on my LinkedIn, and I want everything to be on brand, and I want everything to point back to that [00:11:00] article."

And I wanna be able to do that in 30 seconds or less and have a digital personal marketing assistant that just goes and handles it all. And so I'm building that. and if I get it right, then it could be something really cool. I'm doing it for myself but as I share that story, other entrepreneurs are kinda plugging into it, kinda like what we did with the mortgage business.

And it's not like we're-- we've got 10,000 users or anything like that. There are a few close people. But it's a really cool experiment to, again to be in that startup phase as an entrepreneur, to be like, "You know what? I'm solving this problem for myself, and I'm doing it with the broader perspective of, 'If I get this right, this could be a really fun project that reaches beyond the mortgage industry,'" which I've never been able to do before.

Jeffrey Feldberg: Love that story, and when you think about it, we can look today at the biggest companies. Logos change over time, doesn't. The founder had likely a personal problem, wanted to figure it out, did it so well, they were world-class in what they're doing. [00:12:00] Other people found out, "Hey, Jason, what you did for yourself over there, can you do that for me?"

Or, "I love what you did with the company. How do I do that?" And one thing leads to another, and you're out there changing lives and solving that painful problem. So I know it's still early days and perhaps a data point of one for you right now. it comes to that, though, because for me, not just myself, my biggest failures, by the way, has been putting together the sales teams or the marketing teams.

And oftentimes, I'm still learning, by the way, on the interview side. Maybe you've learned to master it. I'm still learning as I go along, dropping the ball, making the mistakes. Oftentimes, the best result was in the interview, and then it was all downhill from there. The best sales or marketing job they did was an interview with me and that was it. So that said, when you look at what you're doing on the marketing side, what was the biggest surprise or insight or revelation for you of, ah, okay, you know, I always thought it was this, but actually it's that. I should be zagging when I'm [00:13:00] zigging. What does that look like?

Organic Growth Over Hype

Jason Henneberry: Sure. well, I'm a little bit older, a little bit wiser, a little bit ... I'm willing to maybe move a little slower on projects than I used to be. I've done all the things you just mentioned, where like I've raised capital to acquire other businesses. I've built sales teams, fulfillment teams.

I've spent a lot of money, effort, and resources in trying to scale fast. Sometimes that's worked out. A lot of times it hasn't especially when you have multiple projects on the go, it's hard to keep it. For this particular project, I'm in startup mode. I'm really trying to do it very organically.

It's a different approach than I've ever taken. I really am patient with the project. I'm trying to build it so that I will use it for myself. And so every feature, like right down to the, the scripting and the styling and all this kind of stuff, it's, i'm putting a lot of effort into making sure that it just works and that it's a product that I would actually use to promote my own personal brand.

And that is a much different approach than saying, "Okay, I wanna go out and I wanna have [00:14:00] 1,000 users by the end of the year." I'm okay to only have 100 users in 12 months if that's what it is, but I want those 100 users to be get a lot of value out of the system. And so I, my whole approach is if I can make it work for me, then it'll work for somebody else.

I don't think, that's different than let's go build a big business. But over time, I think what ends up happening is if you're you bring on users that just really love the product. and then, and you make it work really well for them, and then they won't go. They won't leave.

And so retention becomes easier. The depth of the relationship becomes easier. And and then eventually you can focus on scaling rapidly or building that sales team or doing whatever. So a lot of what I'm doing right now on the startup side is very organic. Yeah.

Jeffrey Feldberg: Interesting, and at the risk of dating myself, back in the day, it was really my business partner, Steve Wells, who was doing the marketing. This was before social media and the platforms and everything else, and so Jason, it was more old school. [00:15:00] it was an email, which was considered high tech back

Jason Henneberry: Yeah, sure

Jeffrey Feldberg: could be an old-fashioned letter that you put a stamp on and send it out in the mail. 

Likes vs Real Buyers

Jeffrey Feldberg: What's interesting, though, would love your thoughts on this, as I looked at today, it feels as though a generation or two of marketers have drunk the Kool-Aid, and it's not the right Kool-Aid to be drinking because we've been led astray of, "Jeffrey, all you've gotta do is get a zillion likes or followers, and you're set." And it couldn't be further from the truth because th- there's a difference of getting a like or a follower to actually buying, and would love your thoughts on that.

Jason Henneberry: No, 100%. And I think that what y- what you just said is an extension of what I was saying, which is I'm looking for less scale, deeper relationships. And everything I've been able to do in my business, my entire reach has been 15,000 max total market size participants. And that's not very big as, as far as the market [00:16:00] goes for B2B.

The the... I think the misconception is that you need all these followers, you need all these likes. I think the algorithms don't really care about that stuff anymore. If your content's good, if your message is good, the systems will find the right people that should be paying attention to it, and you can build a spectacular business with a reach of 500 people, 1,000 people, as long as they're the right people.

And how do you get to them? How do you build those deep connections? You still need all those tools. You still need to have that social presence. You still need to be doing the emails. You still need to be publishing the thought leadership pieces. But that's all table stakes stuff now.

And then the name of the game is what you said, is how do you go from those early engagements to conversion? How do you move that digital relationship into analog? And that's the secret sauce

Show Dont Tell Content

Jeffrey Feldberg: And so for the secret sauce, what's been some of the biggest aha moments for you?

Jason Henneberry: Biggest aha moments is show don't preach or show don't tell. And my whole marketing strategy around [00:17:00] content flow, which is the app and the system that I'm building, is to essentially show it off, and show it off how I use it for myself. And so you're getting that reach, and you're getting that early engagement, but you're really showing how the thing works.

It's tangible. So for entrepreneurs, like any entrepreneur, what I notice works really well for people, and I've talked to a lot of people who are, building good brand presences and so on, the thing that seems to work the best is when they just show the thing that they're talking about.

That could be a mortgage broker with a pad and a pencil writing out an example on a piece of paper. Could be a realtor walking through a house. Could be a lawyer explaining an actual legal case. Don't talk above the reader. Don't talk in terms of the high-level stuff.

Just get really granular and show your expertise off. And that tends to lead to better conversions because then, someone's watching, and that person has that exact problem that you're displaying, and they can see that you are the gap between their problem and the solution that they have because you've shown [00:18:00] it to them.

You haven't just told them that you're the solution. You've actually shown them that you're the solution. I think that works really right now in this moment of time.

Jeffrey Feldberg: And in this situation, and the Deep Wealth Nation is very familiar with this question I'm about to ask, because my favorite question, it's a bit of a two-edged coin though, because it can be so generic, so high level. "Jeffrey, what are you talking about? Every situation is different. Can you be more specific?" But that said, when you zoom out, two fancy words, Pareto's law or the 80/20 principle.

Jason Henneberry: Sure

Jeffrey Feldberg: to Deep Wealth Nation who are not getting it right. perhaps don't have the expertise like you've had of building multiple businesses, exiting those businesses, having some experience behind you, having that patience that you referenced at the beginning of the conversation. would be 80%... We'll do the glass half full. What would be the 80% of the challenges that probably most founders are having right now on the marketing side that are likely coming from, "Yeah, Jeffrey, you know what? It's these [00:19:00] one, two, or three things. When you either start doing this or stop doing that, most common mistake or frustration or shortfall can likely vanish or go away"?

Tool Overload Trap

Jason Henneberry: One of the biggest problems that I see is that there's so many tools now. There's so ma- There's the AI models, there's all the different platforms, and the promise is that it's going to save you time. But we end up, right now in where we are in the cycle of everything, I don't think we're delivering on that promise.

I think that we are just as likely as entrepreneurs to spend more time, prompting and engaging with a system than it takes to actually solve the real problem. You could just go and do the thing. And a lot of us mistake busy work with being effective, and so I see it in our industry where and we have mortgage brokers that we support.

A mortgage broker's job is to help a homeowner get a mortgage. it's not to prompt AI. It's not to write scripts. It's not to be on social [00:20:00] media. It's not to do all those things. Those things have to happen, but that it, those things aren't the thing that makes you the money.

The conversion happens when you get a homeowner, get a client, and close that mortgage. And a lot of mortgage brokers aren't even doing that. They're so busy doing all this stuff, and they're spending like, five hours on this and 10 hours on that, and building a CRM, and building this funnel and this lead magnet, and all this stuff, and it's not actually making them more effective at their job.

And I think this is probably happening in a lot of different industries. And I do think we're gonna get to a place where all these systems, it'll just be as easy as, hey, you just talk to it, and it just gets you, and it just goes and does the thing the way you want to, and we hit that miracle moment.

But it's not happening yet, and so I think the biggest mistake entrepreneurs are facing is they're spending so much time on all these other things that isn't the thing that actually makes them money, and then they're stressed, and they're depleted, and they're, they're just [00:21:00] spread thin.

And I'm seeing that a lot right now

Jeffrey Feldberg: So it's like the good old saying, "Don't confuse activity with progress." I can be building the best AI prompt in the world or this back-end CRM system or this or that, hey, why would I do that when I can hire someone who can do it in a fraction of the time, free up my time? It goes back to Why Your Business Will Let You Go, book number one, a lot of these principles to have me out there doing what I should be doing.

It reminds me of something. I had a conversation, it's going a while back now, was with a good friend, successful fellow who also helps other business owners. He said, "Jeffrey, I don't get it. I am so much," how can I put it? "Smarter than this one other fellow, and I have a bigger audience. But this guy, the zeros in his bank account make mine look like a rounding error, and he doesn't think, he just does, whereas I'm thinking, I'm not just doing." And so we had a whole conversation around that, and as you're talking about that, it reminds [00:22:00] me of sometimes stop thinking and just do. Just get out there. Done is always better than perfect. How am I doing with that?

Jason Henneberry: You're doing great with that. I fully subscribe to that. nothing beats action. if you had to place a bet on the person who's gonna think through their five-year strat plan and get it right and then go execute, or the person who's just gonna go execute and has grit and determination and is willing to endure more pain by getting slapped in the face and just working through the problems, I'd put my money on that person every day of the week.

Because they will be that much further ahead in the learning in six months because they just went and did it and learned what doesn't work and have adapted to that, versus the person who hasn't even left the start gate who is just thinking about how to do it properly. So I'm 100% on board with that philosophy.

Jeffrey Feldberg: Dreamers dream and doers do, and it just makes all the difference out there. And usually success, believe it was Woody Allen who said, "Hey, success, 90% of it is just showing up consistently every [00:23:00] day and taking those actions and doing maybe I don't want to do it or I don't like doing it, but just doing it, getting out there and being seen."

Jason Henneberry: As entrepreneurs, the successful entrepreneurs, the ones that do we're typically pretty good at build forward, right? Or fail forward, as you put it a moment ago.

Design Backward For Freedom

Jason Henneberry: you have something that needs to happen in front of you, you take that action, and then you solve that problem, and you go and you solve the next problem, and the next problem, and the next problem. And you build momentum around your business. What ends up happening, though, and this is where entrepreneurs could use a little bit of that thoughtfulness and the just take a second and think about what it is you're trying to achieve, what outcome are you trying to get to in your business before taking that action.

It's just a momentary thing. Don't stop the action, but you still want to build forward, but think about the outcome you're trying to achieve. And design the business backwards. You build forward and you design backward from outcome first. And a really good example of a business that designs for outcome is are, like, the airlines.[00:24:00]

Airlines don't go, "Hey uh, we've got this cool idea. We might be able to get people from point A to point B. Let's fire up a website. Okay, they just booked travel. Oh, my goodness, we need to buy a plane. Let's get a pilot to fly the plane." Like, That's how entrepreneurs work. That's the fail forward, right?

And you need that energy for small businesses. Bigger businesses like airlines, they start with the outcome, and the outcome for an airline is the plane always lands. And in order for that plane to always land, we need to make sure that the plane is built a certain way and that the pilots have certain training and the systems have redundancies.

And they build the whole business backwards, right down to the booking of the trip. And so entrepreneurs could use like, the really go-getter entrepreneurs that are just building forward all the time, they end up inadvertently building a business that they can't step away from, and it's because they don't take a minute to pause along the way to design for outcome.

And the outcome that you want as an entrepreneur is you want that freedom, you want the liberty, we become entrepreneurs because we think it's going to help us have a better lifestyle or whatever that promise is that you're [00:25:00] out to get. And oftentimes we just end up building this business that we can't step away from, that relies on us completely, and it's because we never take a moment to think about designing it for the final outcome in mind.

We're just constantly in that action-oriented build forward mode. Very useful when you're trying to get something off the ground or put momentum behind it. Not as useful if you're trying to build a business that doesn't rely on you

Unwinding Founder Handcuffs

Jeffrey Feldberg: And as you're talking about that, if I'm not mistaken, it was right around the start of the book, the quote, "Every business depends on something. Dependency itself is not a flaw.

Dependency is," and usually as the founder, we're the unintended dependency, to your point. I gotta build this business.

I gotta have this lifestyle. I'm gonna solve this problem. I'm gonna help enough people get what they want. Eventually I'll get what I want. grows. We get drawn into the growth and all the issues, and next thing I know, I've got the golden handcuffs. Would love your thoughts on that of, okay, yeah, that's there. How do I begin to [00:26:00] unwind that? And I'm guilty as charged, particularly with my first company, Embanet, the e-learning company. I was the company was me. There's no separation between the

Jason Henneberry: Sure. And you had to rework things in order to step away from that business at some point. You had to have a moment where you were like, "Okay, this isn't gonna work. I gotta reorganize."

Jeffrey Feldberg: in part and it showed up in two different ways, Jason. Before y- you go on with your explanation, just to throw myself under the

Jason Henneberry: Sure. 

Jeffrey Feldberg: don't do this. you know, if you want an example of what not to do, don't do what I'm about to share with you. And so it, came up with hiring a leadership team before we went to market.

You know, Buyers are smart, they're like, "Jeffrey, you've got a great leadership team, wonderful people. The only challenge is they haven't been in the seat for at least three years, and we can see right through this. We see this all the time. They don't have the proven track record, and so we're gonna ding you for that.

As great as your company is, still have some worries." Now, Jason, whether they had the worries or not doesn't really matter. They're always gonna use something to [00:27:00] give an excuse or a reason of why they wanna pay less for the enterprise

Jason Henneberry: For sure. Yeah

Jeffrey Feldberg: then the second thing that happened, it's called a non-compete. And so the next day after the business was sold, okay, now what do I do? Because post-exit Jeffrey was so focused on getting the business, the deal, the exit, the liquidity event across the finish line, I always said I'll get to what I do after the sale Let's just let it happen." And that led to my dark night of the soul, all the mistakes, the frustration, did not get the happily ever after right away. And so it was that dependency that I couldn't take myself out of the business in enough time to build a life outside of that for true joy and fulfillment.

Jason Henneberry: Oh, yeah. Okay

Jeffrey Feldberg: don't do that. Jason, let's hear the smarter view of what to actually do of that instead of what I shared with you. What, What would 

Jason Henneberry: you nailed it. 

Accidental Dependencies Explained

Jason Henneberry: you said earlier every business depends on something, and that's why the, the broad title of the book is Dependency Design. It's not that you build a business that doesn't depend on things, it's [00:28:00] just you wanna do it by design, not by mistake. And most of us as small business entrepreneurs, we end up building dependencies by mistake.

So a really good example of building a dependency by mistake is you have these different buckets in your business, like revenue, right? Sales and revenue, and then you have fulfillment, and then you have operations and processes. So you have these different buckets. And let's say, let's just focus on revenue for a second.

When a business is young and growing you are the business. You have to be. It's your idea. There's no staff. There's no processes. You're out there grinding it. So you're every part of that business, and you are pushing forward. And then as the business grows, you might bring on a sales team. That sales team, let's say they're out there, and There's a problem with a sale, and so revenue is at risk. What we tend to do as entrepreneurs is we will jump in to save the day, right? So the salesperson calls and says, "Hey, Jeffrey, I got a problem. This key account is going sideways." Jeffrey goes, "You know what? Let me have a chat with them." And you have [00:29:00] that skill set or whatever it is to save that account.

What happens in that moment is we think it's, we think it's leadership. We think it's strong, guidance for the business. But what happens is we teach the business that we are the thing that gets called on to solve those critical moments. And so the next time there's a problem like that, guess what happens?

Phone rings. Jeffrey gets called in. You gotta go solve the problem. And the business learns that you're the solution. 

Founder Dependency Trap

Jason Henneberry: And so dependency design is about not making that mistake, not jumping in as an entrepreneur with some kind of heroic effort to save the day or solve the problem, which we do so very well.

But to actually design each part of the business so that it can solve the problem without your intervention, and that's a whole other conversation, but that's really what we wanna do so that the business actually does run without you

Jeffrey Feldberg: And so in that instance, and you're spot on with that, it's like the frog in boiling water. We don't intend for that to happen. We don't [00:30:00] even notice when it does happen. Most founders are like myself, Type A personality. I'm that adrenaline junkie. I like that rush. Yeah, I came in, I saved the day. So sales team now calls out, "Hey Jason, Jeffrey, we're gonna lose this customer.

We're gonna lose the deal. What should we do?" Instead of us jumping in, what does that look like? Because it's so much quicker and easier. I can imagine Deep Wealth Nation saying, "Jeffrey, can just jump in there. Let me have that one phone call. It's not a big deal." It's quicker to do that. We really need the deal and the revenue than not having me involved, but there's a cost to that.

And so again, every business is gonna be different and the culture will be different. But that said, some general best practices that you can recommend that's worked

Jason Henneberry: Sure. 

Handing Off Discretion

Jason Henneberry: It's easy to see this, ... So task assignment is actually fairly easy for most entrepreneurs. Eventually we figure out how to systemize and operationalize a business if you're successful. maybe between the, 100,000 to $500,000 [00:31:00] range, not so much is needed, but you hit 700,000, a million dollars in revenue, you're probably system-oriented.

You've got some processes and at least one or two team members. And so we're pretty good at task assignment But what needs to happen in that moment when revenue's at risk or something's not going to plan. So task assignment works well when you have a defined plan, everything's going to plan, the system, the people, the processes, everybody knows what to do.

that dependency, those things carry the business. It's when something doesn't go to plan. Those are the moments that we notice as entrepreneurs that we step in, because the system, the process, or the people, they don't have what is needed in that moment to solve that problem, and so it gets escalated and lands back on your desk.

That's actually what happens. And so you don't just hand over responsibility and accountability and judgment in one moment. What you want to do is you want to contain the blast radius, and you need to hand over that accountability in small increments. 

Sales Team Pricing Rules

Jason Henneberry: So let's say it's your [00:32:00] sales team and you're selling a $1,000 widget, and you wanna maybe start by saying, "Hey, look, if these situations come up, you have the discretion to knock the price down to 500 bucks.

You don't have to call me. You don't have to do anything." You're containing the blast radius, right? In my world, I ran a sales team. This is before Tango, but my whole mortgage team, I was the big lead gen. We would do 1,000 leads a month, and our revenue per file was anywhere from three to seven or $10,000 per file.

So material. And our lead costs were 750 to $1,000 a file. That's just what it cost us to close a client. And then we had salaries and all that for the sales team. M- I gradually gave my team the ability to make exceptions all the way down to that $1,000 range, And they learned that you know, if you encounter this friction point at, early in the sales process, you only bring it down to here.

you have discretion to here. If you have to go lower than that, just walk away. It's not worth your time. You haven't invested any time in it. But if you're, like, 90% of the way through [00:33:00] and you encounter that friction point, then, you have this much more discretion, because you've already done the work.

Let's just close that revenue. Let's bring in that $1,000. We get our marketing costs back, we can go buy 10 more leads, and we wash and repeat, right? And so I trained my team to understand the, those judgment calls that I would make intuitively as a founder to save the day. Those are the softer points.

And I gradually handed over responsibility and accountability in the sales process to a point where I never had to talk to a client ever again. And they made the right calls along the way. But I didn't just say, "Here's your job, and you figure out how to make the call." That wouldn't have ended well. I gradually handed over that responsibility over time.

And so it's a little bit more intentional. And that's just one example. Yeah

Jeffrey Feldberg: example though, and let's walk through that, and then I want to circle back to another point for the marketing business that you're working on. What I like about that, though, is you explained the why to the [00:34:00] team, I found it so important when someone understands why you're doing what you're doing, they can relate to it.

It becomes that much more important. And so you had the patience, "Okay, here's why I'm gonna say what I'm saying or why we're gonna do what we're gonna do here. I want you now to take this and run with it." So I would imagine from your mindset perspective, you're saying, "Hey, I don't want to be doing this for the rest of my life. Let me take the time now, as painful as it may be, as time-consuming as it could be, I'll do some early examples. If I have the right people, they'll learn quickly. We can document this. We can systematize it. We can get it built into the culture. They'll get it right, and if they don't, we can talk about that."

So you're very intentional, explain the why, and then through examples, and I'm sure it didn't all go in a straight line. There were probably some

Jason Henneberry: Oh. Lots of mistakes

Jeffrey Feldberg: we lost that one. Let's talk about that and learn about that," or, "Hey, this never should have come back to me. Let's talk about that again." So you did that, and you put that out there. 

Delegate vs Abdicate

Jeffrey Feldberg: [00:35:00] included, when I speak to other founders, and I can relate because I've done the same thing, our mantra at Deep Wealth is delegate, automate, or eliminate.

Jason Henneberry: Love it

Jeffrey Feldberg: a fourth option that sometimes we don't realize, and it's always a, a fine line there. Sometimes as founders, we abdicate. And so it's, "Yeah, Jason, great. Welcome on board. Welcome to your new responsibility. Here's your goal. Here's the outcome. Here's the vision. I'll talk with you this time next year. Let me know how it goes." I completely walk away. I don't own the process, and of course, it's gonna be a disaster

Jason Henneberry: It's not gonna work

Jeffrey Feldberg: they they don't get that. opposed to I've delegated, but I'm micromanaging. I'm checking in every step of the way, and now everyone is miserable. I'm miserable. The person on the other end is miserable. So from a founder's perspective, what did you do for yourself, particularly during those challenging situations that had you wake up the next day, "Okay, new day, new opportunity.

Yeah, yesterday [00:36:00] was terrible with what happened. I'm gonna learn, rinse, repeat, move forward," that had you come out the other end successful? Because you said, "Hey, not that I don't care about our customers. I do. Just at certain levels, I'm not the one that should be speaking with them, and I haven't done that level since."

So what did you learn that you can share with us?

Three Buckets Framework

Jason Henneberry: So there's more than three buckets, but in this context, there's three buckets. So the first thing is we talked about task assignments really easy. Let's just keep focus on sales and revenue. There's lots of areas of the business and there's different examples. Sales and revenue is the example we've been talking about.

Task assignment in sales and revenue is something as simple as, okay, lead comes in, you call the lead in 15 minutes, and you have this conversation, you ask these five questions, you pre-qualify, you move to application, whatever. So that's task assignment. Really easy to ... You can actually document that and give it.

And that's something that someone can learn really fast. We're all good at that as entrepreneurs The next part is discretion, which is what I just talked [00:37:00] about, which is containing the blast radius when things don't go to plan. And so you don't want to just abdicate. You want to gradually give them a more discretion, more power, and then you want to teach and guide along the way as you learn those lessons.

So you start with $100 discretion, and you get to a $1,000 discretion, till you get to a point where they really understand the why behind certain decisions and all that stuff that we just talked about. 

Incentives Drive Behavior

Jason Henneberry: And then the next part is incentive and motivation. It's the flip side of the balance sheet. Now you're not just giving something away to the customer in awkward situations or you, but you have the incentives and the motivations and how does the person that you put in that role win.

using my mortgage broker sales example, we always had a base comp and some kind of performance threshold, and that performance threshold for a salesperson were based on revenue tiers. If you do, You might have a... I'll just use round numbers [00:38:00] just so that it's helpful for anybody building a sales team.

Let's say their base salary was $5,000 a month. Their first threshold before they make a bonus is 10K, and the reason for that is because at 10K, I have enough money operationally to cover my lead cost and my systems and pay them a salary. At 10K revenue, though, as a business owner, I'm treading water on that staff person.

I've got the lead flow covered. I got my systems. I'm good as long as they bring in 10K. So that's the first threshold. Then at 15K, they get a bonus, and they call it 10% of the incremental amount. So they get, 500 bucks as a bonus on top of their base. And I get most of my profit in that next 5K.

But then I really ratchet it up, and then at 20K, they get half of the next increment, right? And so now, so what they care about is they care about hitting that 20K threshold because they're now making five grand plus 500 bucks plus a $2,500 bonus. And as a business, [00:39:00] I'm covering my nut. I'm getting my core profit on the f- on the next 5K, and I'm splitting the difference with them, and I now have roughly around, 7,500 bucks in profit on that 20K revenue.

You got a good business model. So that's just an example, right? That salesperson cares about hitting that 20K threshold because if they hit 19, they're on that 10% bonus plan. They don't make anywhere near what they're about to make. And so they push hard. They will apply those discretionary rules at, in the way that maximizes profit for the business because they want to, they care about every single dollar that comes in, and if they need that extra 1,000 bucks at the end of the month, they're gonna take it.

they're gonna bring in that file that's the holistic thing that you need for a salesperson. That doesn't, you don't have to apply that comp model. That's just an example of what we did. And that gives them the tasks, the roles, the defined responsibilities. It gives them the power of discretion, and it gives them the motivation and the incentive.

And if you get that mix right, you don't have [00:40:00] to police. You don't have to micromanage. They'll just go do the job in a way that is optimal for the business because it's optimal for them

Jeffrey Feldberg: And Deep Wealth Nation, were you paying attention to that? Because it was oh-so subtle, yet important because Jason, what he was sharing, now this is specific to his business, your business is going to be different, but he's built right into the key performance indicators, into the bonus system, into the commissions, into the structure. There's a built-in incentive when I get to this level or here's why I want to get to this level, the world is great, instead of having to piecemeal it along. Really love how you've done that, and you've baked it all in, and it also goes back to when it's data points, it's no longer personal. "Hey, Jeffrey, you really suck at that.

You dropped the ball here. What's going on?" "Jeffrey, the KPIs were terrific last month. This month they're in the red light area. What's going on here? What changed from when we last met till today?" Makes a very easy conversation. Nothing's personal with that. So with all of [00:41:00] that said, hindsight's always 20/20. Jason, a bit of an unfair question. As you're building out this marketing system, I know it's right now only for you. That said, I know in the back of your mind you're just a smart guy, and you're ambitious, and you're talented. "Hey, if I can make it work for me or when I make it work for me, why not have this work for other people?" How are you building into this marketing system, company yet not named or determined for future services, whatever it's gonna be, how are you building into it right now? 

Building Content Flow

Jeffrey Feldberg: Okay, I'm taking myself out of the mix. Yeah, I'm figuring out right now because I have to, I'm the only one, but when it goes to market, I'm not gonna be the go-to person.

It's gonna be systematized, or it's gonna be this person here doing that there or this position there figuring all this out. What's that like right now in the planning stages?

Jason Henneberry: I'll tell you. So it probably came across like I'm very early on this business, but I've actually been working on it for over a year now, and we have a couple hundred users on it in my world. I'm curious in expanding my [00:42:00] reach to, beyond the mortgage industry. But we have a couple hundred mortgage brokers that are using the system already.

What we did is we started with one feature. That's it. And we came out and we said, "Hey, look, you're busy being a mortgage professional, and so let us write your articles for you." And this is going back 18 months now. And at the time, we realized we could help people write their blogs faster because AI was coming on the scene.

And so we started with that. And then we delivered on that promise, and then we started taking feedback from our users and they would say, "Hey, you know what? I want my articles to be a little bit more glass half full," or, "I want to sound a little bit more like this. And by the way, I'd love a, carousel post for my social media that points back to the article, and I'd love a script."

And so we just kept building the features in. and so when I say I'm building it for myself, where we ended up is we ended up with this suite of features that's article forward where all your other ancillary marketing content points to it, like an email to your database, social posts, a script for your video reels, [00:43:00] that kind of thing, and everything points back to the article.

Overbuilt App Fix

Jason Henneberry: But we got so much feedback around the nuances in the voice that we ended up, and this is a cool thing, we ended up making the app so complicated because you could customize it that nobody knows how to use it anymore. And so when I say I'm ... This is a real problem I had, and I had this problem like three months ago.

And my intention was 90 days ago to start talking about this amazing app that I built because I had proof of concept and we've got a few hundred users and it's going really well. but then all of a sudden we hit this road. We hit a wall, and we overbuilt the app, and now my existing users are starting to complain.

They're like, "We get that it's supposed to do all this stuff for us, but we don't know how to use it." And I'm like, "Oh, crap. I can't promote this." And by the way, I don't know how to use it. I've forgotten all the features I built. So I'm like, I've built this thing so that I could use it to talk about it and promote it, and it would make my life easier in promoting the app, and I can't even use it as the founder.

That's really where I was 90 days ago. And so what we [00:44:00] decided to do is we buried all the features in the app. And for anybody who's, building an app or building a system for your team or trying to do something for your immediate team or to sell something to your whole business, there's a lesson here.

I think the future of interface, and we're seeing it with ChatGPT just brought out Dots and there's Grok Bot and Meta has Muse, and all of these AI systems, they're burying the features and they're moving to like an agent assistant type relationship personal bot. And so we did the same with ours, and turns out this is a pretty good idea 'cause people like it.

Maya Chat Interface

Jason Henneberry: So the work that we just did in the last 90 days was we built Maya, which is short for My Assistant and we buried all the features and now we just have a chat interface. And Maya is your personal marketing assistant. And so now you just show up and you say, "Hey, Maya, I want an article that talks about this, and I want an email and I want a campaign," and blah, blah, blah.

And she'll just go and do all that stuff. Maya knows how to use the tool to build all that stuff on brand, in your voice and so [00:45:00] on. When we're done this podcast, Jeffrey, and I get a copy of it, I'm gonna take the transcript from it, I'm gonna give it to Maya and I'm gonna say, " build a marketing campaign around this."

And I'm gonna send it out to my database and I'm gonna do a video and I'll put it on Instagram, and it'll just build all those assets for me around what we talk about today, and it'll be on brand for me. So I'm really excited about that. But there's a lesson there for anybody building anything is don't think anybody wants another app.

I don't think anybody wants another feature or setting to adjust. I think we are rapidly moving to a towards a world where all of that stuff is gonna be in the background and we're just gonna wanna say what we want and then we want the outcome. We just want the thing that we ask for. So if you're building anything, that's an important thing right now, I think.

Jeffrey Feldberg: And Deep Wealth Nation, so many takeaways from what Jason just shared. So firstly, we heard Jason say, "I got caught up in this and I got excited," but I took... Not to put words in your mouth, Jason, and you can always say, "Jeffrey, on base or off base with this," but you're saying, "Hey, I got caught up in the excitement as well.

[00:46:00] I took my eye off the prize. With this new marketing service, what do I want? I wanna make it effortlessness. I wanna make it easy that not just myself, but down the road, a paying customer can do more with marketing, become more effective, more efficient, more successful than they could on their own." And you listened to that, and you got creative. It's what I'm now hearing this term a headless experience,

Jason Henneberry: Yeah

Jeffrey Feldberg: behind the scenes with artificial intelligence or super intelligence, whatever you like to call it these days, it's a headless experience. There's no longer the interface. It's, "Okay, Maya," in this case my assistant, "create me an article. I had this podcast interview with Jeffrey on Deep Wealth Podcast.

I wanna send it out to my network. Here's my outcomes. Go ahead and do it." You don't care that there's 1,001 features that can help you do it. You just, this is the outcome. My eye on the prize is this, get that done. Deep Wealth Nation, are you agile enough to make those changes in your organization of, "Hey, [00:47:00] we got our eye off the prize here.

Let's get it back on. Oh, this means a complete redesign of what we've been doing." And so really admire you for that. And Jason, thanks for being so open and vulnerable with that. And so with that said, as you're now working with a, a few hundred potential clients that are early on in the system, and that's the other thing, Deep Wealth Nation, you don't hear Jason saying, "Yeah, I've got to get to a gazillion followers and 10 gazillion likes before I'm thinking of creating this app."

And yet, no, I'm not gonna wait. Let me find some other people who I'm far enough along, they have the same problem, I can get their feedback early on. And you probably told them, "It's not gonna be perfect. There's gonna be some speed bumps along the way. But if you're okay with that, I can help you." And you began to do that, and now you're changing, you're morphing as things go along, and you're making it better. So Jason, if you fast-forward on this marketing side again, I know we're all over the map here. There is a method to the madness.

Jason Henneberry: Ja, ja

Jeffrey Feldberg: the m- on the marketing side, once you begin to scale, get this out there, it's made a difference for [00:48:00] you, what's the vision for you as you look to the marketplace now, whether it's B2B or B2C, whatever form it takes with the marketing service that you're gonna be putting out there? What's the big vision? And then again, what are you deliberately reminding yourself of? "Hey, Jason, don't do this, do that," because eye on the prize. I don't wanna have the golden handcuffs. I wanna be able to scale this and still have my freedom, my time, my lifestyle.

Jason Henneberry: I can probably bring this up a bit. 

Vision and Impact

Jason Henneberry: I know we've been talking about Content Flow and Maya, and I appreciate that. That's just my personal project, but I would imagine some of your listeners have their own projects, and they're trying to solve problems in their own business and maybe for broader audiences.

And I think the lesson in what I just mentioned is we should look at our processes and our interactions with our clients and where are the opportunities, where are we causing more friction than we need to? And we live in this wonderful time right [00:49:00] now where we can actually remove that friction.

It might take a little bit of effort. It can be hard on you behind the scenes in order to get there. But wherever those friction points are for your customer, if you can alleviate them, if you can go headless, like you said, Jeffrey, I think those are wonderful opportunities for any business. And I just happen to be doing that with marketing and trying to solve that problem.

My big vision is I would really like to do something-- Not that I don't have a substantial business. Like we're in the mid eight figures in revenue. It's a good business. I would like to break out of this my sphere of influence, and I would like to do something at a broader scale.

And I think that solving this problem, if I can solve it for myself, if I can solve it for the people in my world, if we can get the message right, and we can make Content Flow work for really any entrepreneur, that we, might stand a chance at being able to do that and having a bigger impact on the world.

Because I think that this problem isn't just uniquely mine or uniquely [00:50:00] the mortgage industry's. We all have it. Getting our message out, getting our voice out, doing it in a way that doesn't burn a bunch of our personal time, that it's efficient, that it's on brand. Those are real, tangible problems that are worth solving.

So I'm hopeful to be part of that process and help other entrepreneurs solve that for themselves.

Jeffrey Feldberg: And Deep Wealth Nation, what Jason is sharing is such a valuable takeaway. He's tuning into the world's favorite radio station, WII.FM, the what's in it for me. Not as Jason, as his client, as his stakeholders. What do they want? They don't care about me per se. It's what do they want? How do I help enough people get what they want, so over time I can get what I want?

And you've done that with your other businesses that were successful. You grew them. You either have them or you exited. It's a formula that time and time again, regardless of the technology, it's been around. It'll continue to be around because it works.

Back to the Future Advice

Jeffrey Feldberg: So that said, let's go into wrap up mode, and [00:51:00] it's our tradition here on the Deep Wealth Podcast. Jason, it's really my privilege and my honor, I ask every guest the same question. It's a fun question. Let me set this up for you. When you think of the movie Back to the Future, you have that magical DeLorean car that will take you to any point in time. So now, Jason, imagine it's tomorrow morning. You look outside your window, the DeLorean car, it is curbside. The door is open. This is the fun part. You're now gonna hop in and go to any point in your life, Jason, as a young child, a teenager, whatever point in time it would be. What are you telling your younger self in terms of life lessons or life wisdom, or, "Hey, Jason, do this, but don't do that"? What would it sound

Jason Henneberry: Besides buy Bitcoin and, and every IPO in the tech space? Just believe in yourself, have the confidence that you will be able to figure it out, and maybe don't be so eager. My younger self was really eager, and I made a lot of mistakes by pushing hard fast. I think that's just something that comes with age and a little bit of wisdom and [00:52:00] getting kicked in the teeth a few times.

I think that's it, is that just you will get there eventually. and I gotta be honest if I didn't try to do more, I would probably have more. And just going deep down. Every single idea I've had 'cause I've, tried a lot of things, and some stuff has worked out, and some stuff hasn't.

But every single idea I've had has ... there's some version of that has worked out in the world. It may not have worked out for me, but they weren't bad ideas. And so all of those things that I played with along the way could have been the thing, had I just focused all my energy on it. And I'm fortunate enough that I had a few things that have worked out, and I think I learned that lesson early enough to get to where I am, which I'm grateful for.

But there's a lot of spinning my wheels, just trying this and trying that and trying this. And If you have something and you believe in it, just go deep on it. Just give it your all. Don't have it half-ass it, as Matthew McConaughey puts it, and it will probably work out. Just believe that you have the, what it takes to work through all the problems that are gonna face [00:53:00] along the way

Jeffrey Feldberg: So some terrific advice. Believe in yourself, know that it's gonna work out, and if you're really passionate, if you believe in it, go all in and burn the bridges. Look to say, "How can I make this happen?" Get that out there. See where it takes you. Failure is part of the process, for better or for worse.

Oftentimes it's for the better with that. It's some great advice. 

Where to Find Jason

Jeffrey Feldberg: And Jason, that said, if someone in Deep Wealth Nation, they wanna reach out, they wanna have a conversation, even become part of the early days in the community with the marketing, with the Maya, with the whole AI system that you're putting together of how I can leverage my solution from a marketing side, where's the best place online to reach you?

Jason Henneberry: For the Content Flow stuff, you can just go to contentflow.media. Thanks for giving me the opportunity to say that. And there's, free trials and all that kind of stuff. You can plug in and start using it. for me personally, my handle is Jason Hanaberry. You can find me on Instagram, LinkedIn, pretty much anywhere, @jasonhanaberry.

And [00:54:00] soon you're gonna see a lot of me as I use my app to build more brand presence. there you go. Thanks, Jeff. Appreciate that.

Jeffrey Feldberg: I absolutely love that. And so Deep Wealth Nation, go to the show notes. It's all there. It's a point and click. It doesn't get any easier. And Jason, that said, congratulations. It's official. This is a wrap. As we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe.

Thank you so much

Jason Henneberry: Thanks, Jeffrey 

Final Wrap and Subscribe

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. 

What did you think? 

So with all that said and as we wrap it up, I have another question for you.

Actually, it's more of a personal favor. 

Did you find this episode helpful? 

Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? 

And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

Are you ready for it? 

The dramatic pause. I'll just wait a moment. Drumroll, please. Subscribe. Please subscribe to the Deep Wealth podcast on your favorite podcast channel. When you subscribe to the Deep [00:55:00] Wealth Podcast, you're saving yourself time. Every episode automatically comes to you, and I want you to know that we meticulously craft Every one of our episodes to have impactful strategies, stories, expert insights that are designed to help you grow your profits, increase the value of your business, and yes, even optimize your post exit life and your life right now, whatever you want that to look like.

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So all that said. Thank you so much for listening. And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's continue this journey together. And from the bottom of my heart, thank you so much for listening to this episode.

And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. 

Thank you so much. 

God bless.