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Sailing off the Cliff

Stephanie Holmes faced condescension when she floated the idea of deviating from just selling financial services. She wanted to help people change their spending habits, structure their debt, and have the life they want, and she had to start her own practice to do it. She later sold it when she started The Money Finder, of which she is currently the CEO. She chats with Clate and Scott about naysayers who tell her she’s a “stupid little girl,” seeing challenges as adventures, business inspiration, and how to grow a team and make sales happen without her direct involvement.

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Mentioned in this podcast:

  • “Banker to the Poor” by Muhammad Yunus
  • “The Icarus Deception” by Seth Godin
  • “Pitch Anything” by Oren Klaff
  • “The Little Books of Value Investing” by Christopher H. Brown


Stephanie Holmes: Those types of "You can't do this. That is stupid. There's something wrong with you." And sometimes it would even be, "You're a stupid little girl," and I've had people say that to me, and I think, "Huh, okay. Thanks for the rocket fuel."

Clate Mask: Yeah.

Scott Martineau: That's great.

Stephanie Holmes: So yeah, I think if it hadn't been so condescending, I may have been more mild in my reaction.

Clate Mask: That's Stephanie Holmes from The Money Finder sharing her secrets to overcoming doubters. Keep listening for the rest of her story. This is Clate Mask, Co-founder and CEO of Infusionsoft, on the Small Business Success Podcast.

[Music stops]

Scott Martineau: And I'm Scott Martineau, a Co-founder of Infusionsoft.

Clate Mask: Stephanie, how you doing?

Stephanie Holmes: Uh, wonderful.

Clate Mask: Good. We're excited to be with you. Thanks so much for joining us.

Stephanie Holmes: I'm too excited. It's cold here in Halifax.


I'm jealous of your sun and your cool sound studio, so thank you for bringing me back into your world, if only for a few minutes.

Clate Mask: You bet.

Scott Martineau: Well, Stephanie, why don't we start out, and if you can share with the listeners your story. How did you get started? What gave you this crazy idea to get into business yourself? And just kinda give us the brief overview and foundation of what your business is all about.

Stephanie Holmes: Sure. Well, in 2001, I got really sick, and I had two choices: live or work, but I wasn't gonna get to do both. So I packed up my 1996 green Dodge Neon – it was fancy –

Scott Martineau: Oh baby.

Clate Mask: Awesome.

Stephanie Holmes: And my dog – it sounds like the beginning of a country song. And I drove back from Alberta, back to Nova Scotia, and I was gonna be a vet – ta da. But that's not quite what happened. It turns out that I was really good at sales. I got recruited into the financial services industry, and they said I was gonna help people, and then they proceeded to teach me only how to sell stuff. And I thought, "Well yeah, I get that insurance helps, that investments help; I get that. But that is not what I thought I signed up for.


What about when people make $100,000.00 or more and they don't know where their money's going? Or what about the college kid that's taking over the family farm that doesn't know how to manage a credit card? What about the stuff – the stuff that people live in with their money every day? Where's the learning for that?" And I literally got patted on the top of my head like I was the office Cocker Spaniel by my manager. He leaned over and he said, "Aren't you cute? You think this is about helping people."

And that was it. I just – there was an internal snap. It may have been audible. And I went to 20 of the clients who I knew best, and I said, "Listen, we're gonna figure this out; you in? I wanna figure out how we can help people change their spending, manage the structure of their debt, and have the life they want from the money that they've got. And I do not wanna take 'no' for an answer, and so I'm gonna get you to do things, and we're gonna experiment. We're gonna test it, and I need you to be really honest with me, even if it hurts.


Even if it's hard." And so those 20 people helped me build the process that became the thing that I was known for in the industry, and I did a lot of media and things like that. But it became clear pretty quick that I could help a few hundred people. But financial advisors who had heard me speak, or read my books, or read me in media, they were coming up and saying, "Hey, I wanna do what you're doing too." And then I thought, "Ah; I wonder if I can take what I've figured out and get other people to do it too."

So I sold my financial services practice, 'cause I'm not one to test it and then jump off the cliff – I'll just jump off the cliff. I'm like, "Hey, everybody, let's go here. There's a cliff." So I sold my practice in 2011, and I tested my theories in live training, and in 2013 we turned it into a nationally accredited in Canada financial services designation. We made a software. We coached them.


And there are now over 300 advisors in Canada who can literally repeat what I did, and they're impacting thousands.

Scott Martineau: Wow.

Clate Mask: That is awesome. Congratulations. I love hearing the fire that you had when someone in the establishment kind of patted you on the head –

Stephanie Holmes: Yeah.

Clate Mask: Said, "Oh, isn't that quaint. Isn't that nice." Because that fighting against the establishment is so often what gets entrepreneurs to say, "You know what, stick it. We're gonna do something different, 'cause I know in my gut, I know in my heart there's a better way." And that story that you shared I know resonates with entrepreneurs that are saying, "Yeah, I have a bigger reason why I'm doing this. And of course we wanna have a good financial outcome, but can't we do that in a way that's great for people in the process?" So congratulations; gee, that's awesome.

Scott Martineau: So Stephanie, what do you think would've happened had that moment not happened? You went from being a vet to being a Cocker Spaniel.


You know, if like you hadn't had that moment, do you think you'd be owning your own company today? Was it kind of in you from the start, or did that help push you over the edge?

Stephanie Holmes: I think that a lot of things – I've learned to listen to it better now, so it still took me years from then. I mean we're talking that's a ten-year point from the pat on the head to the, "Hey, I'm selling my practice, and get out of my way and I'm doing this myself." So I think that those types of "You can't do this. That is stupid. There's something wrong with you." And sometimes it would even be, "You're a stupid little girl," and I've had people say that to me, and I thought, "Huh, okay. Thanks for the rocket fuel."

Clate Mask: Yeah, exactly.

Stephanie Holmes: So yeah, I think that if it hadn't been so condescending, I may have been more mild in my reaction, and I think I could've given up easier. So I now look at like this morning; that's why we see challenges as adventures.


This morning when I got a call and we had some complications with our new sales plan, instead of getting all angry and just totally going, "Ah, this is the sign. It's not gonna work. I should give up," my attitude is, "Okay, we were upset for eight seconds – that's enough. Now it's an adventure. What are we gonna do with it?" And I've learned to do that faster the more I've discovered that every time I take that stance, we grow. So yeah, I think that if there was no adversity, I don't think our muscles build up as strong.

Clate Mask: Yeah; powerful.

Scott Martineau: Yeah; that's awesome. So you told the sort of beginning and then the current state. Take us a little bit on the journey of what – you know, I'm guessing it wasn't all roses, kind of keeping with the topic of adversity. What was the point, maybe there's been more than one, but maybe what's a point that stands out as sort of the low point in your experience as a business owner? Tell us what that was like, and just help us understand how you got through that.

Stephanie Holmes: Yeah. So we do have low points; I just like to keep them brief, learn from them, and move on, 'cause you can wallow in those things for a long time.


So there's been a couple. Getting sick and losing my job, and I worked in agriculture, so they can actually fire you for being sick – it's illegal everywhere else – so those types of things happened. But as far as the business, from the time I sold my practice to where we are right now, lots of things have been massive challenges. First of all, we work in regulated industry, so we had to get large corporations, who have a lot of regulatory pull, to give us a chance.

To listen to our training and say, "Yes, this is approved. The advisors you've trained can actually do what you taught them." And I can remember early conversations of, "Well yeah, but who came up with this? Well, no, no, no, it can't be just you – no, no, no, no, no. No, no, what organization, what body of people, what operation –"

Clate Mask: Supreme experts – "Who were these people who came up with this brilliance?"

Stephanie Holmes: Yeah, who were these people?

Clate Mask: "'Cause certainly it wasn't you," right?

Stephanie Holmes: Yeah. So fast forward. I was talking to Assante, which is a rather large firm in Canada. I was talking to one of their leads in compliance.


And business development was also on the phone, and they said, "But who are the people that develop this?" and I thought, "This is now funny to answer. Back in the day, it would give me the shakes." And I said, "I did." And they said, "No, no, but who actually came up with the ideas?" "I did." "Who recorded the audio?" "I did." "Who made the slides?" "I did." "Who made the techniques?" "I did." "Who built the concept for the software?" "I did." And they were like, "Oh, you did." "Yeah, I did." So those things are sometimes challenging.

But I think the biggest one for us was right before we went to Elite Forum, we had success. We had made sales, but we just couldn't see how to attract the right people to grow the team, and how do sales happen without me having to have my hands in them? And we're still figuring that out. We get better and better at it all the time, but that has been the biggest challenge. And we go through big highs, especially when we go do workshops and we do live sales.


We've learned to manage the monster high, 'cause we come back and we're like, "We can do anything. Get out of our way. Rah," and we're so excited. And then we're like two weeks' home, we're like, "Oh, that would be readily sub. I'll just go lay down." So we've learned to manage the road high – we call it that – and we've learned even with salesppl we have to be really careful to manage that road high, because it feels like, "Hey, I can go make 30 sales in a day. How come I can't do that on the phone?"

Clate Mask: Yep.

Stephanie Holmes: It's a totally different beast; you probably have experienced that, Clate. You come back, you're like, "Yes, we did it." And then you're like, "Oh, other stuff is still hard."

Clate Mask: Yeah.

Scott Martineau: "Everything should be like this."

Stephanie Holmes: Yeah, those things. And too, we've had some business partners fall out. There's actually two companies; one is trading, and one owns the software, and we had some business partners want out in a hurry last summer, and we just had to come up with cash fast.


And that was really hard, because it came right before a series of workshops, which are really expensive for us. And they pay, but it takes two months before we recoup actual revenue. So it's just debt for two months when we do it.

Clate Mask: Yeah.

Stephanie Holmes: And then we had our biggest annual client event, which is very expensive for the company size we are right now, but very important to our culture and the community. And those three things went bang, bang, bang; they went August, September, October. So by the end of October, my team was watching me want to put a paper bag over my head permanently, and I had to go seek out some smarter people than I am who had been through tougher stuff than this, and I had to get them to kinda talk me down from the freak-out. Because that still happens, and I think as long as we're growing, that's probably still gonna happen.

Scott Martineau: Yes.

Clate Mask: Yep.

Stephanie Holmes: I just have to get better at managing it. But those, some of the low points have really been around people, and cash flow, and sales.

Clate Mask: Yeah. Thanks for sharing that; just taking people through that journey a little bit I think is encouraging, because everybody faces those kinds of things as they're growing their business.


So tell us was there a point when you said, "Okay, we're gonna make it?" So a high point, where you said, "You know what, this is really gonna happen," and you have that feeling of "there's nothing that can stop me."

Scott Martineau: Stephanie, think about that for a second. I actually wanna interject something before we move on, because I – Clate, don't you feel like this story of going out to the regulatory bodies, does that not remind you of the Muhammad Yunus story in Banker to the Poor?

Clate Mask: Totally. Totally.

Scott Martineau: Have you read that book, Stephanie?

Stephanie Holmes: Is that the Accelerate Through the Wobble?

Scott Martineau: No. That is the iterative creation of micro financing.

Clate Mask: In Bangladesh.

Stephanie Holmes: I have not read that book.

Scott Martineau: In Bangladesh. It's amazing; you should read it. It would be a huge confirmation to the stories you're sharing with us. But he's basically sitting there in Bangladesh; he's an economics professor. And he walks out teaching economics to these people that are dying on the streets in complete poverty.


And he thinks, "I'm gonna go end poverty," and he starts by finding these destitute women in Bangladesh, who are getting just totally taken by these predatory lenders. And he says, "We're gonna discover a model of financing that will work for them." And today we look at micro financing – in fact, that's one of the causes that Clate and I and Infusionsoft are really passionate about investing in, and we partner with a provider.

Clate Mask: The book's called Banker to the Poor.

Stephanie Holmes: Banker to the Poor.

Clate Mask: And it's all about Muhammad Yunus and the amazing industry he created to end poverty. It's incredible.

Stephanie Holmes: That is filled with emotion.

Scott Martineau: And the core of most of the story is basically what you were sharing, which is he'd go to these banks and they would say, "You've gotta be kidding me. There's no way. What's the collateral?" right? And he had to just go up against every wall that he could possibly imagine. He just kept going and going. It's just powerful.

Clate Mask: In a country that didn't recognize women's rights at all.


Stephanie Holmes: Yeah.

Clate Mask: They weren't allowed to enter contracts. They weren't allowed to vote. They weren't allowed to do anything, and here he was creating an industry that bucked every trend in the culture, and created a way for women – and ultimately, anybody – to get a loan. But primarily women, and they pay back at a 98 percent-plus rate. I mean it's just amazing. But you'll appreciate it partly for what you're doing in financial services, partly for who you are as an entrepreneur and what you're creating, some of the garbage you've had to trudge through and plow through in order to accomplish what you're doing. And really, any entrepreneur who's had to just fight the establishment to go create something different that people didn't think was possible will love the book. But it's a great one.

Scott Martineau: And I hope that the listeners hear your example. You basically give yourself eight seconds, so you've got enough time for a rodeo ride to be angry, and then it's on to, "Okay, what are we gonna do about this?" I think it's brilliant.

Clate Mask: The rodeo ride – I like that.

Stephanie Holmes: Yeah.


Scott Martineau: So let's go back. Clate asked you – tell us about the opposite end of the spectrum. When did you have this moment when you just felt like you're on top of the world and everything's working out?

Stephanie Holmes: Yeah. So it's not that there aren't moments, of course, of stress or pain in the midst of any day, or any week, or any month; it happens. But I ran across my office there because this – it says, "Pitch yourself." It is the box from The Icarus Deception, which Seth Godin wrote. Seth's one of my favorites; we've interviewed him for the blog. And last spring we were really trying to figure out – we'd come up with this workshop idea. It was starting to work, but we were having trouble getting big companies.

'Cause what we're trying to do is get them to pay for them and we'll go do them, because it brings value. You get CE credits, community education, all this fun stuff. And we were sitting there, and I said, "You know, we can't do all the workshops under our own steam, 'cause that'll cost us $100,000.00."


And then I looked up at that box, which sits on my bookshelf, and I went, "Yes, we can. Yes, we can. We just have to price it so that it sort of breaks even or comes close. We're gonna pick ourselves." And the whole team just said, "Yeah. Yeah, we're in. We're gonna do that, too."

Clate Mask: That's great.

Stephanie Holmes: "That's gonna work." So I could tell two years ago that this was gonna work, but it wasn't until I realized in that moment where we were discussing what we can't do, and I went, "Wait. Yeah, we can pick ourselves." Like everything we don't think we can control, we might not be able to control in the moment, but we do have ultimate control over the result. We just have to decide to. And this year, I would've loved to seen more of a point made about it; I think you guys should harness it again next year. At the bottom of all your ICON 16 slides, it said, "Decide to succeed." And I love the fact that the Latin derivative of the word decide actually means to cut off.


So in order to decide to pick ourselves, we had to cut off all the potential corporate financial services companies that might want to have a workshop. We had to say "no" to them to be able to say "yes." And so that is, I think, the most ultimate confidence that our success is imminent and consistent and happening, is that ability to realize we decide if we're gonna succeed.

Clate Mask: Yes, so let's pause there, 'cause that's golden. I think that – you know, I asked a question, what was the high point? When did you know you were going to make it? And your answer was essentially, "When we picked ourself and cut off a bunch of other courses, a bunch of other avenues that might have been the traditional ways to get there." And I think those two points, what you're saying is first, you really looked at yourself in the mirror and said, "We can do this."


"We've got it." And then you took action where you let go of some of the traditional ways that others might do it, and in doing that you came out the other side feeling like, "Yeah, we can absolutely do this." And that's a story that we hear frequently among entrepreneurs, and we can identify with it ourselves. I remember early on in like the end of 2004, we were just starting to get our product out there, and we were relying on smart people that had a lot of influence to sell our product.

And we basically went and had our version of the road high, where we went out at an event and we sold, and we didn't have to hire a gun. We didn't have to have somebody else do that. And we came away just like, "We can do this. We've got this. We don't have to look for someone else to kind of –" for a long time, people have been saying, "Well, you guys just create the technology, and then we'll sell it for you." And it was like, "No. No. We can do this. We've got it."


And that created an independence, and it created a confidence that coming out of it – that was at the end of 2004 going into 2005, and that's really when things started to turn for us. And we were like, "This is gonna be – this is really gonna make it. This is gonna be an awesome thing." So thank you for sharing that with us.

Scott Martineau: Feels to me like, at least in my experience, that business owners struggle from a couple of things. One is just fear. I mean you've talked about a lot of jumping-off points, right, and it just feels like we're literally sailing off the cliff. And you've gotta have the courage to do that, and I really appreciate you sharing those examples. I think the other is sort of this conformity. So we might look around and think, "Well, everything I've seen in my experience would lead me to believe that I need to do it this way and I've gotta conform."

And I think that's one of the biggest travesties, I guess, of the way that business owners choose to run their business. You literally – like we're in our own business because we have the ability and the desire to go do things the way we want to. And I actually think it's a huge advantage that a small business owner has to go out and just do things differently, you know.


And show up in a way that causes people to say, "Wow, there's something different about that way that that company's doing business." Anyway, so fantastic points.

Clate Mask: Well, and that's what we talk about – and you know this, because in Elite Forum we talk so much about the intentionality of your creation, and not just kind of going with the flow of things, but actually being very clear about your purpose, your values, your mission, why you exist. And I love watching what you've done as you've taken that content and that experience from Elite Forum and have just totally run with it. So you're doing amazing things.

Today we can look at it and say, "Oh, you're doing great things as a stage four seven-figure business, and you've got big visions of what you're up to and what you're going to accomplish." But what would you say to people who aren't yet to that stage four, that elite place where very few businesses get to?


But you've got there; what would you say to them if they kind of have their eyes set on becoming a seven-figure business, but they are still in that place of doubt, and not sure that they're gonna be able to get there? What characteristic would you encourage them to develop, or what piece of advice would you offer to them?

Stephanie Holmes: Yeah. So the first thing – I know exactly what you're talking about, 'cause I remember the first time we heard anything about Infusionsoft, and we had got a little bit introduced to Elite Education. And my attitude was, "Oh, well that's great for them. Of course they can do that, 'cause they have all this success now." And I realize that it was only turning off that voice that actually helped me listen.

So if anybody who's listening right now is going, "Oh, well that's easy, because they have 16 employees, and they've already made money, and they've already figured this out. And they've already got regulatory approval, and they've already done all these crazy things. Therefore, I can't do it," turn the "yeah, but" off.


Because all it's doing is cornering you. So I've had so many people – this is something we mention from the stage. We mentioned it in the breakout. I mentioned it to everybody who came up to me and said, "I'm just running a little tiny business, and poor little old me doesn't have any employees, and I can't get someone else to use Infusionsoft for me, or I can't leverage these technologies." And my answer to that was, "Hey, do you know that I had a virtual assistant."

When I bought Infusionsoft, when we launched the designation, she was actually a full-time employee by that time, but only for a few months. But I had one person who I paid four hours a week, or six hours a week – something crazy like that – and she was a local company. She was an employee of the virtual assistant company, so I had no responsibility for her, but I had hired them. And I literally phoned her and said, "Hey, I bought this thing. You're gonna learn how to use it, okay?" If you don't need 15 people to make something work, or 500 people to make something work.


So I would say first of all, turn off the "yeah, buts."

Clate Mask: Love it.

Stephanie Holmes: Because – yeah. I can learn something from Amazon, and the way they think. I can learn something from – you guys had Oren Klaff there, brilliant at ICON. If you haven't listened to his book, do that. Very exciting stuff about the human brain.

Clate Mask: Oren's got a book, it's called Pitch Anything, and it's all about having the mindset to sell effectively whatever it is that you're selling, so Pitch Anything is that book.

Stephanie Holmes: Yeah, Pitch Anything, Oren Klaff, he's awesome. And he loves M&M, so I love him even more. But yeah, and I think the core competency, the thing that will help you succeed, is actually one of our core values, and that is to be forever tenacious. When I was little, my mom read me these books. They were called The Little Books of Value. I don't know if anybody remembers them; they were white books.

Clate Mask: Yeah.

Stephanie Holmes: And they had Louis Pasteur, and "Rocket" Richard.


And they were about – I remember "Rocket Richard" is about being tenacious, the value of tenacity, and that stuck to me my whole life. And even if you watch popular shows like Shark Tank, they'll tell you the entrepreneurs that succeed are the ones that fall down and pop up; they're not the ones that don't fall down. They just pop up really fast. So it's tenacity; I think that is it. If you can be not ruthless, but relentless, and incredibly tenacious, you will get exactly where you're trying to go.

Clate Mask: Love it.

Scott Martineau: I love it; it's awesome.

Clate Mask: So tell us, I wanna hear a little bit more about the transformation of you, right? You've got this team about you, but my experience as business owners go from the phases of small business success that you've gone through is that there becomes work that you've gotta do on yourself as the leader of the company. So maybe take us on your leadership journey; what did that look like?

Stephanie Holmes: I am a ball of clay.


Like if I think I know what I need to be, I'm wrong. I've learned that. So my leadership journey would've started when I entered Strategic Coach in 2013. This is pre-employees. I'm sitting at my first session, I'm like, "This is awesome," and my program advisor comes up to me and she goes, "Did you love it?" I said, "Yes." She goes, "Are you excited?" I said, "Yes." She's like, "So are you gonna do what you know you need to do now?" and I'm like, "No." She said, "What?" And I said, "I don't wanna hire people. I don't want employees. Eww."

And she said, "Oh, oh, oh, no, no, no, no. You might not need employees, but you need a team. You can't do this by yourself. You can't become better at the thing you're best at if you're trying to do the bookkeeping, which by your own description, gives you hives. So you really need to stop." So it has been a constant evolution in letting go.


And then when we went to Elite Forum, I think it was the first thing you said, Clate. I think it was, "Entrepreneurship or leadership is an exercise in letting go." And I was like, "Oh, again? All right." So really, we've gotten to the point that I went from doing everything – so I recorded all the webinars. I made the web pages, which is pathetic, if you ever saw them. I made the PayPal buttons. I went and did the talks. I negotiated my speaking fees. I booked all my plane tickets. I did everything. We went from that to me letting go of first, operational-type stuff, so the stuff that I was most incompetent at, and skill set that was most accessible.

So sales is a harder one; we went to operational stuff first. So I hired my VA at the time; she's now our VP operations, but I hired her to be my assistant. She started taking all the stuff that I wasn't good at off my plate, so we've had a consistent evolution of that. So it's gone through phases where then I handed off the sales.


I'm still involved in the sales, but the actual phone sales, I handed those off, and we started growing who is now our sales leader. And I started then handing off booking of travel arrangements, 'cause those also give me hives, but I'm a control freak, so it's like this big battle. We have it figured out now. It's a big battle, so it was slowly but surely letting go of things, one step at a time, one person at a time. And so every quarter, we do – it's from Coach – we do a unique ability exercise with all of the team members.

So when they have their one-on-one strategy session with their leader, only the leaders report to me, so I have three people report to me. We don't have ever more than five reports, so like one day Baranzi was talking about that, 'cause I hate more than five; it's too much. So when they report to me, I do their session with them, and then I go to my coach and I do mine for me. And what we're now finding I have to let go of, which I'm terrified of, is the live workshops. I can't raise capital for our company and be the leader I need to be if I still do the live workshops.


It is too much of a stretch. So I think it's that evolution of letting go; those things that either I got them down to a process that could be taught to somebody else, or I just realized I was completely incompetent and hired somebody who was.

Clate Mask: Ah. Thank you for sharing that. So many gems in there about the process and the journey that you go through as an entrepreneur as you grow your business, and just the way – congratulations on the way that you're relinquishing control gradually, and wrestling with that control freak that's inside of all of us as entrepreneurs, and learning how to let go of things appropriately. Congratulations on building a team around you. You know, I think there was genius in there about 16 employees and you've got 3 people that are reporting to you.

So many times entrepreneurs are carrying way, way more of the weight on their shoulders. So just thank you for sharing that, because there were a bunch of things in there that I think are really brilliant points for entrepreneurs that are trying to grow to that seven-figure business and beyond.


And so I just appreciate you sharing all of that. And you know I'd love to – we congratulate you on your success. Scott and I are sitting here listening to your stories. We remember things that we went through. We hear very familiar refrains of challenge and frustration for entrepreneurs all over that are going through this. But congratulations on doing it your way. Congratulations on creating the thing that you knew in your heart was going to change the world for people.

And I'm so excited for you 'cause I know you're just getting started; you've got so much out in front of you, and the vision that you have is really cool and exciting. So I guess one thing we'd love to know is do you have any questions for us? Is there anything that we could address for you that might be helpful?

Stephanie Holmes: Yay. Yeah, definitely. I would love to know a better way, or help me not make some of these mistakes myself, on building our sales.


Our sales model away from me is probably the toughest thing I've ever had to try to figure out. And a lot of the people on your team have been absolutely wonderful for us at Elite Momentum. Elizabeth Pitt gave us some great feedback on how we position jobs, and we had Christine Rogers is amazing. I don't know if you spend much time near her, but she literally gives off energy. She's amazing.

But I don't know how to support my leaders, or do I hire somebody else whose job it is to build out sales? It is the number one stressor for us right now. 'Cause if we put me on the road, we can make sales, but then the company's growth halts and waits for me to make sales, and that is becoming obvious that that's not a good thing.

Clate Mask: Yeah, I hear you.

Scott Martineau: So help us know a little bit more; what's the core problem?

Stephanie Holmes: So the core challenge is it's a complex sale to a wounded sales force.


I don't know if you've ever seen – have you ever spent any time around horses or dogs?

Scott Martineau: Yes.

Stephanie Holmes: Put them in a narrow enough pen, what do they do? They bite each other, and the biggest, toughest one bites the next one, and the next one, and before you know it, everybody's got a big bite mark. And so the financial services industry, you get bitten a lot. You get rejected, the press hates you; and so when someone tries to sell you something, you're like, "Aw, yes – smaller guy. I'm going to bite him." So we have a lot of challenges with salespeople that have the experience to be able to see that for what it is.

They're just testing you. They're just trying to see, "Do you actually care about me, or are you just trying to get me, because enough people have done that to me." So the challenge is it's a complex sale to a sophisticated or well-sales-trained or sales-hurt professional, who feels the need to defend themselves immediately, and it's a real challenge. And just getting them in, attracting them, is challenging as well.


Scott Martineau: Does your sales leader attract the kind of mature and seasoned and capable sales rep that can handle the bites from those that the rep is selling to?

Stephanie Holmes: Not yet, because I end up having to drag him on the road with me to do workshops; which means his time frame to actually get really into it, it's these little narrow windows of time, which is just I don't know how to work around it. So I haven't given him the runway to even see what type of person he'll attract with some time. It's always in a rush, always in a rush.

Clate Mask: Yeah.

Scott Martineau: So I have three thoughts; I'll share two, and then it sounded like you might have one, too. But one thing is maybe you need to double the gauntlet that you're putting your prospective employees through.


And I don't know that there's any way to get out of the fact that there's just gonna be – I mean it's the nature of the sales position, I think, is that it's gonna be challenging. So while it's so tempting, you have a need right now. You've got a need to create sales and so forth – I understand that, but that's one recommendation I have. So how can you make it harder? How can you make sure that you're really putting people through the ropes and investing the time to make sure that you're bringing the right people?

And of course, I know that you know this, but I'll just say this for the listeners. Of course, complete dedication to making sure that you're bringing on people that are in line with the core values I think is absolutely critical. That's one line of thinking. Another recommendation I'd have – and I don't know how much of this is the issue but how much of this could be solved by better marketing. That is, creating leads that are predisposed to having a different type of conversation. Sometimes great marketing can tee that up, so that the sales conversation just starts from a completely different place.

Stephanie Holmes: Yeah.


Scott Martineau: Yeah, so –

Stephanie Holmes: 'Cause to me it's clear too, Scott, it's not that everybody's like that. But you know how when ten people say something nice to you, but one person says something mean, and then all you hear over in your head again is the person that said something mean? I think that's what's actually happening is one person hyper-reacts to them, and then they're terrified. And when they don't have any financial services background, they don't feel like they can stand up for themselves, or we're not supporting them in a way that's giving them that.

'Cause their leads are pretty good quality, but it's just like the, "Well, I had five conversations today, and I'm gonna choose to dwell on the person that was not happy to hear from me." But I mean anything that gives us better quality leads will help. But yeah, I find that sometimes that is very much subjective; we just need them able to handle that one, so they can rock it on the next ten calls.

Clate Mask: Yeah, so I got a couple quick thoughts for you. The first is if you rewind what you just said a moment ago, you said something really important: "When they don't have any financial services background." So I would encourage you to find some people who have some financial services background and are in love with your cause.


Because they were the Cocker Spaniel that got patted on the head, right? So I know that's hard to find; I know they probably tend to be a little more expensive than the reps that you're currently paying. But I would really look hard to find somebody that fits that. Second thing is you need to create credibility in your sales reps through you and your sales manager, and I'm sure you do that from the marketing side, but think of it in kind of the middle of the funnel.

At the top of the funnel, you're using your credibility to bring – I know your style of marketing. You're bringing people into the funnel, potential prospects into the funnel, but maybe at the middle of the funnel there's an opportunity to create more credibility for your sales reps. One way you might do that is through a weekly webinar where you or the sales manager is leveraging the expertise and the credibility.


But you're also transferring that expertise and credibility to the sales reps, so the sales reps can then take that sale from the middle to the bottom of the funnel. There's something in there where you are currently leveraging your expertise at the top of the funnel; your sales manager needs to be able to leverage his or her expertise in the middle of the funnel. And they might need to borrow your expertise occasionally, but you wanna get out of that expertise-lending business in the middle of the funnel as quickly as you can.

And your sales manager should be the one doing that, so if your sales manager isn't comfortable on a group demo or a teleseminar, webinar style of a setting in the middle of the funnel, then you need to have the conversation with the sales manager to develop that skill, so that he or she can extend that credibility to his or her sales reps.

Scott Martineau: Well Stephanie, thank you so much for spending time. Your energy is infectious.


I wish people could see you and have the experience that we're having with your little on-fire energy, and we just appreciate you sharing your stories of tenacity, the lessons you've learned as you've grown your business. It's just an inspiration to be with you.

Stephanie Holmes: Thank you. Right back atcha.

Clate Mask: Yeah, seriously, congratulations on your success. It's awesome to see. We're excited for the next stage of your growth. We know that growth just brings new opportunities, new challenges; they're exciting. I love the way you're tackling them. Congratulations on what you accomplished to this point, and we totally salute you for the Small Business Success icon that you are. The way people look to you and see what you're accomplishing is really inspiring, so thank you. Thanks for being with us.

Stephanie Holmes: Awesome. Thanks, guys.

Scott Martineau: Thank you.

Clate Mask: All right, thanks, everybody, for listening in to the Small Business Success podcast.

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