Hilary Rushford started a side gig as a personal stylist while on unemployment insurance and built it into a seven-figure business in four years. Soon she was getting as many requests for advice on how to build a business as she was for advice on style, and she began offering courses on social media marketing and entrepreneurship. Her professor + therapist approach creates lasting change in her clients’ style, business and life.

In This Episode

Hilary Rushford’s entrepreneurial career began with helping women feel good about themselves through their personal style, and it’s since evolved into empowering women in their businesses and lives. Modern Ontrapreneur sits down with Hilary to discuss her unique “therapist and professor” approach, how she’s able to create more space for herself while also taking on more projects, and the importance of being honest and authentic in this modern entrepreneurial era.


Topic Timeline:

1:45 You Need More Help Than You Realize

It’s not due to a lack of intelligence, but you aren’t the only person to ever do this so get the help and advice of others as often as you can.

6:17 A Therapist and Professor (Education and Empathy)

Taking complex, confounding topics and making them easy to understand

12:40 Growing the Team

Bringing in leaders to fill high positions has opened doors to focus on other projects.

16:55 Make More Space For “Me”

Delegating current assets of the company while also not picking up new projects that may compete with the aspects you want to focus on now

19:52 Helping Woman Heal

Empowering women to feel good about who they are, how they look and how successful they can be.

22:49 Simplifying, Authenticity/Vulnerability, and Honesty

Being a modern entrepreneur is about inspiring people’s dreams but being real about the journey without sugar coating it too much.

I think we’ll spend a lifetime being fascinated by and trying to really just set women free.

– Hilary Rushford

Show Transcript:

LR: Welcome to Modern Ontrapreneur. I’m Landon Ray and today I have Hilary Rushford, who started a side business as a personal stylist while on unemployment insurance and built it into a seven-figure business in four years. Soon she was getting as many requests for business teaching as she was for style, and she began offering courses on social media and anti-hustle entrepreneurship. Her professor + therapist approach simplifies the complex and creates lasting change with her passion for more joy and less overwhelm in your style, business, and life. Here it is.

HR: All of that is true.

LR: Thank you so much for being here, Hilary.

HR: Thank you. Thank for having chairs in my favorite color of peacock blue. I really appreciate it.

LR: You’re welcome. We did that just for you. Four years ago? No, it’s been longer than that.

HR: Now it’s been about six and a half years, but we had a big financial shift right around four years.

LR: Amazing, isn’t it, how that happens? You build and build and then it turns into something.

HR: It still feels very weird. Honestly, we were wandering around the hotel and my business partner was like, “Isn’t it cool to see the behind the scenes?” I said, “Actually, I used to cater so often that…..”

LR: Just having flashbacks.

HR: This is where I was normally hanging out, so it’s those little moments that are cool to be like, “Okay, I would have been catering here and I respect all of those people.”

LR: Glad not to be doing it.

HR: I didn’t feel like I was using my talents. I’m so thankful that’s not what I’m here for today.

LR: Yeah. If you could think back, then, to six and a half years ago and give yourself a tip, that caterer or that unemployed girl, I guess, what would you tell yourself that would have made that, I mean, honestly four years to seven figures, it sounds like you did a pretty good job. But still, we all struggle. What would’ve made it easier?

HR: Yeah, it was way more miserable than it needed to be.

LR: Yeah.

HR: Even though it sounds like a short period of time, that’s all of the time you were in college. That’s an excruciating time to be so overwhelmed and feel so alone, so I wish in hindsight that I’d had a fairy godmother that had said to me, “Get a therapist and get a business coach.”

LR: Interesting.

HR: You need more help and it’s not a measure of you not being intelligent enough, because I thought, “Well, I’m an A+ student, I’m pretty savvy, I’ll just read all the things, I’ll go to all the webinars.” And I was really diligent, I took action, but you’re just so in it, it’s like if you’re going to become a new parent, you read all the books.

LR: Yeah.

HR: Like yes, we have that instinct as parents, but so many people have learned so many wise things that you don’t necessarily have an instinct to know. Like, kids have peanut allergies, so you’re really thankful that you read the book that told you that and the year that we 6x’d our revenue in year is the year that I started getting help and realizing this isn’t getting any easier any time soon, so I got a business strategist and a business coach, and HR consultant and I up leveled our bookkeepers.

Just so many things, bit by bit and even when I started going to therapy, I thought, “Well, it’s not like she’s going to be able to help me with business advice,” but I realized, no, it’s just people advice. It’s the same thing as being in a conversation with your spouse when you’re trying to figure out why do you and your project manager keep miscommunicating?

LR: Yeah.

HR: That’s just about humanity, she didn’t need to understand anything about funnels to understand, “This sounds really exhausting, and you’d like to make it easier, so let’s give you some tools for that.”

LR: Yeah, so finding a business coach, especially after you’ve been cracking at something for years, you feel like you are familiar with the problem. You may not know something, but you know enough to know what doesn’t work and it sometimes feels like you’re bringing somebody in and you don’t want to go over the same old problems. How do you pick somebody? There’s a million and one business coaches. How do you make a good decision about that pretty important role?

HR: I think it’s a few things. I think one, it’s trusting your gut. I really have become more and more a proponent of when I don’t really feel like I should hire that person, or I’m not super jazzed, I tend to be like, “Well, I’m probably trying to be too much of a perfectionist, or maybe my expectations are unrealistic.” But the people that I’ve met that have made such a difference, it was just an instant yes.

LR: No brainer.

HR: So I think that’s a big part of it. I also think it’s looking for people, so my first business coach was someone who was doing the exact same kinds of things that I was doing. Online marketing, info product, but was doing it on a more successful level. I knew that. I knew it wasn’t just smoke and mirrors and also in that case, I felt very invested because he was someone who wasn’t taking on business coaching clients. It was kind of a hobby project. So I felt all the more so like I need to be doing my homework, making strides, so that he stays emotionally engaged, because this is such a win win.

He’s giving me stuff and it’s working and so I think it makes me want to be a better student and when I see someone that is so excited that I’m doing that they want to keep pouring in. You realize that’s kind of more reciprocal rather than, you could have a brilliant coach, but if you’re not really doing anything, they’re kind of like, “I don’t know if this is really worth it, I’m just less excited.”

LR: Yeah.

HR: And he also had been someone who had naturally poured into my business. The same thing when I came to bring on two business partners. One of them had kind of been a mentor of mine for a few years and every time we talked it was like we clicked, we were so excited. He loved what I was doing, he just poured out all these free tips and so there was also just that energy of knowing they were excited about me and my business and we just jammed really well together regularly. So yeah, let’s take the next step and make this more formal and beneficial for us both.

LR: Trust your instincts on that.

HR: Yeah.

LR: So what do you feel like your unique skill set is?

HR: As you mentioned in the intro, I feel like I’m a therapist and professor. My dad is a PhD professor, I always thought that’s what I would go into, get my masters, teach at a university. And so I’m really good at teaching. It happened to be choreography and tap dancing before I came into this industry and now, whether it’s style or social media, my strength is taking things that can confound very bright individuals and making it really simple, in a way that isn’t condescending, but where some 40 year old VP at CNN says, “Why has no one ever told me that about these body shapes? You’re right, you’re completely explaining why I like all of those dresses on my body and I don’t like all of those. Why has no one ever said this before?”

So I think that, and really just owning more of that, but I also think the therapy part that pretty much everything we do, I just have so much empathy for how hard it is to run a business, how hard it is to be a woman as far as the negative thoughts and the insecurity and the desire to feel beautiful, so I think I share really vulnerably about those things. I’m clear about what I don’t share about in my personal life, so I don’t feel like I’m oversharing, but I’m willing to be vulnerable in those areas, ’cause I think that’s how we grow and heal is a combination of education and empathy.

LR: So you work with individual clients or groups?

HR: I don’t anymore. I used to and out of that I realized “I’m teaching everyone the same thing. If I could just film this, then I could reach thousands of people at less cost to them and make it easier and more enjoyable for me.” So we have one course on the style side, and three on the entrepreneur side.

LR: Interesting. Under the same brand?

HR: Under the same brand. Yeah, which I’m really passionate about. I believe that you can create what I call an umbrella brand if there’s something cohesive in it. So, ultimately, whatever it is we’re doing, I’m being a professor and a therapist and they’re about having more joy and less overwhelm. Whether that is in your closet or your approach to Instagram or your business in general, there’s really a cohesive theme that I’m just saying, “These are the things that have given me more joy and less overwhelm as a woman and as a entrepreneur, so I’m going to keep sharing them.”

So I think there can be a cohesive message over time without people feeling, and I think it’s only when they are disparate, and you’re like, “Yeah, so I’m a doula, and then I also have this pottery business and I also teach Pinterest.” And you’re thinking, “What do any of those have to do with anything?” But whenever people say, “Oh, my businesses are too disparate,” no one’s ever given us push back of, “Well, why would you be qualified to teach Instagram?”

They look at my Instagram. “Why would you be qualified to teach about anti-hustle entrepreneurship?” Well, they read my Instagram, and they saw me go on sabbatical for four months and they really see me walk the walk, so I think that’s the other part of authenticity, when people are like, “Well, makes sense you started teaching it. It’s clearly what you’re passionate about.”

LR: Yeah, and does the style part of the thing feed into the entrepreneurship stuff? I can imagine, you mentioned the unique challenge that women have with their self-image and they’re concerned about looking good or being right or whatever, and entrepreneurship is such a beat down in those areas in general, and I can imagine you could use looking good, like feeling the part, as a way to bolster ourselves for what it takes to succeed.

HR: Yeah, I think that that is so true, that there is a tie in. I think right now where we find … I was just listening to you talk recently about segmenting your lists and really testing to understand what it is you’re interested in, so we had just done that with our Instagram students, and found out that they’re number two, like why are they taking our Instagram class? Number one, they want to double their Instagram following and number two, they want help starting their new business.

And so I think there’s kind of stages of things that we need money to keep a business afloat and yes, we need confidence and motivation and these other things, but I also want to make sure not to kind of sugarcoat and distract, “It’s all about the right dress,” and these things, if the reality is they don’t have a business that’s really viable. People aren’t really buying it, the product isn’t exceptional, they don’t understand the basics of marketing.

So I think those things kind of come in time, and we do certainly have entrepreneur students that then also take our style class, but I think it just really is important to me that I’m not sort of selling, “Oh, have the perfect dress and it’s all going to make sense,” when it’s the product isn’t there, the foundation that you know it needs….”

LR: But it makes sense, it works for you, anyway, to have these two totally separate things that, because they’re a reflection of who you are and people just get it about you and it’s authentic and they’re digging it.

HR: Yeah, and right now, it’s really one supports the other. And we feel like the style side is really the larger mission side for us. I mean, half the planet is women and it doesn’t matter if you are thin or wealthy or emotionally evolved or successful, women still struggle with not feeling comfortable in their skin, feeling insecure, so all of these things and yet, because we want to help on such a mass scale in that way, right now our passion or entrepreneurship, which also everyone on the team shares, we kind of look at that as the financial driver that lets us to do things…..

LR: Do your mission.

HR: …..that are not as profitable. Like writing a book and selling it at a low price point and things like that.

LR: Got it, awesome.

HR: So aso behind the scenes, we actually see them intertwined as the one makes the other possible. Even if our students, right now, they’re kind of a separate journey, but our team is really clear. That they’re one forward trajectory.

LR: Got it. What is working for you right now to drive business? How are you getting new clients?

HR: So a couple things. One, I brought on business partners, which I don’t know that that’s right for everyone, but for me, it has absolutely changed everything. I just got to a point where between the creative and the marketing and the operations, me being the lead on each of those was just unsustainable and there’s no way that I could go and write a book and be doing morning television and speaking on the style side with other things going on, and so truly by the grace of God and providence, the three of us came together in this very serendipitous way, and it’s like I tripled myself overnight.

And so there is a leader on operations, a leader on marketing and with that, we’ve simultaneously been able to get things going with the book on creative, get things much more organized on operations, and then the biggest part really is getting our evergreen funnels up and running, which now of course, you just want to kick yourself and think, “Why did I not do this earlier?”

LR: Yeah.

HR: But it takes so much work. We have three people pretty much full time: our Ontraport genius, and our Facebook ads girl, and now basically our chief marketing officer. The other partner, that’s what they’re doing full time. I barely even talk to them except for on our team meetings and they’re off making the business so much more profitable because that’s all their worried about and they’re able to really focus on all of those little metrics that you can geek out on that I’ve heard you talk about with…where’s the weak part in the funnel and that seems low for industry standards, so how can we get that up there? First and foremost, didn’t have the bandwidth to do that, but also, that’s not my zone of genius. I mean, I geek out about it, it’s fun, but it’s not the thing that I can be the best in the world at and so to think that I’m going to go off and write a best-selling book on the style side and be in there tinkering with my Facebook ads, just doesn’t make sense. So really it’s been growing the team, which the final part that’s really underlying that, that I’m really passionate about and sharing about vulnerably in a lot of ways is the emotional health component that came with making that possible, and I kind of use that term loosely.

You know, Alex Rodriguez said after his year sabbatical from baseball, he learned how to stop being a jerk. So people can use it in different ways, but acknowledging that we’re all so flawed and so far from perfect and then that gets amplified when you have a team of people around you that are seeing you non-stop, at your worst, in a stressful environment and so I really just spent so much time just trying to heal in different ways.

Slowing down, becoming an essentialist, going on sabbatical, going to therapy, all of these little things to really become someone who could be more calm and secure, because that’s what it required to bring on those business partners and have total trust, totally be on the same page, just kind of have that business soulmate connection. If I had been as stressed out as I was three years into business, they quickly would’ve said, “You seem like a nice girl, but this is just too intense.”

LR: Yeah.

HR: And so I’m realizing more and more, and I always want to point that out so that people aren’t like, “Oh, it’s just the Evergreen funnel, or oh, it’s just the business partner.” Because it really was the work that allows for those things in time. If I’d had those ideas three years ago, it wouldn’t have worked. It’s not that I just didn’t think about it.

LR: Right.

HR: But sometimes it’s having to have that long tail game that really takes quite a few years to have the wisdom and the humility to learn these things. We shouldn’t look back and think, “Oh, such an idiot that six months in I wasn’t figuring that out.” I don’t have kids, but I so describe it as parenting. Just part of the process. You’re going to do your best and grow along the way.

LR: Yeah. Absolutely. So what is your growing edge right now? What are you struggling with? What do you want to learn next? What are you going to figure out next?

HR: Yeah, I think our focus is just making more and more space for me to be able to go write the book and go on press tours and do speaking, all those kind of things to grow the brand that it is very challenging to extricate me from the day to day to get it, and something in our inbox that we all think, “That’s sounds so cool, let’s say yes,” and really have the wisdom to say, “Okay, but does this compete with our first priority? How much work is this really going to take?” And not just be like, “Oh, we can probably knock that out in a day.”

So a lot of it is about that wisdom and discernment as a team to all say … Essentialism by Greg McKeown is one of my favorite books and he researched it because he was interested in why are high performers not living up to their potential and it’s in large part because the more you grow, the more that opportunities come your way. So of course, we get more emails with more cool stuff that we want to say yes to more, and yet really having to be so clear, and getting everyone on board, giving the whole team permission to be like, anyone can raise their hand and say, “Are we sure that we should do this?”

‘Cause the book is the first thing on the mission side, and the Evergreen is the first thing on the money side that supports it, so is this a bright, shiny penny that’s distracting us? And I think that that’s where we have a lot more room to grow and it think that hopefully we’ll look back in six months or a year and think, “Oh my gosh, this is so spacious.” And therefore we’re having more impact by doing less.

LR: Good luck with that.

HR: Thank you.

LR: I’m not sure that it ever gets more spacious.

HR: I know, it takes such intention.

LR: It does.

HR: It’s not easy.

LR: And I think that that’s one of those things that you do learn from again, getting the smack down a few times. When you take on the hundredth project that you probably shouldn’t have taken on, you’re like, “Okay, really we have to stop responding to these things and stop saying yes to those people.” It is a good lesson, for sure.

HR: Yeah, I heard a public speaker the other day say, “I want to say yes to everyone. I don’t want to lower my rates for everything, so I’m not in control of any of those decisions.” He was like, “My assistant and my wife do everything, because I don’t have any willpower.” So I think it’s even figuring out who is your person that’s like, “If I give her this, she’s going to want to do it, but I know that should be a no, so I’m just not even going to give it to her.”

LR: Yeah.

HR: And when are the things that you say, “Okay, well, that seems like a distraction, but it’s actually with the brand that we want to do our book tour with, so it’s planting a seed, so this one actually is worth it.” And getting the whole team on that mentality, I think is really strengthening us.

LR: Good. So you’re obviously closer to the beginning of your career then the end, but if you can kind of imagine yourself 20, 30 years from now, looking back on your career, what would you like your legacy to have been? What would you like to have really built and be known for?

HR: What I’m really passionate about it helping women heal on how they see themselves and their beauty. I think that what I had no idea was going to be my mission when I started out as a one-on-one individual stylist was having that vulnerability in closet after closet with these women that were, as I said, so beautiful, or successful or wealthy or emotionally involved and that every one of them had these visions of themselves that were just not what I saw, not what other people saw and that it actually took so little in order for them to feel empowered.

I think about it non-stop with my niece and my partner’s kids as we look at those girls at three or at 13 and the comments that they’re making about themselves and just realize how it is so wired into women to desire to feel beautiful, even when you think, “We protected my three year olds from everything, where are they getting this from?” And that just absolutely carries over. And I think that that is so powerful, even worldwide. It looks very different in terms of how much money people are spending on clothes and things like that, but I do think that it is a very universal experience.

The desire to feel beautiful, to struggle with that, where does that come from and that’s ultimately the conversation that I think we’ll spend a lifetime being fascinated by and trying to really just set women free. I think when a women really, truly feels beautiful, I see it our students. I mean, they just go from zero to 60 in what they’re able to accomplish. And they’re renewing their marriages, and they’re pursuing PhDs and they’re starting businesses.

So much strength comes from giving yourself permission to play or feel more beautiful or be at peace with your body. So I had no idea that’s what I was starting out to do. I really did just want a side job in my acting career to not have to cater anymore and make some more money. But I just had no idea how much it was going to affect my heart and just see that these are not the conversations that we’re having in women’s magazines and it’s quick fixes and seven must-haves.

So that’s what my whole team is really on board with that vision. Including the men, the men have been so convicted by seeing the student’s stories and talking with their wives and their daughters about it and realizing, “Man, I didn’t think, as a man, I was going to join a company that this was our mission, but now I get it and am excited to be a part of it.”

LR: That’s amazing. So we’ve named this thing Modern Ontrapreneur, and the point of that is to try and shine a light on what it is to be an entrepreneur today, in this moment when things are changing so quickly, and there’s all sorts of new opportunities for entrepreneurs, but also maybe some new responsibilities that come with that.  What do think it means? What are those opportunities and responsibilities today?

HR: Yeah, I think that on the one hand, we have so many opportunities these days with apps and software, it’s like it’s only getting faster, and so that essentialism that we talked about before of anchoring in that maturity to say, “I’m not going to try to be an influencer on every platform; I’m not going to try to do everything. But I’m really going to be, what am I good at? What am I passionate about? What does my girl or guy want?”

So I think simplifying is so much in this day and age, when because there’s so many entrepreneurs, there’s just everything under the sun you could come to Ontrapalooza and leave with a notebook full of ideas, but you can’t do all of them, so what are the ones that you say, I call it the creative candy shop, you just shove it all, you’re going to have a stomach ache and go into sugar shock and not get anything done.

But if you’re like, “Okay, wait, that. Live stream video. I have an acting background. Live stream video I can do better than most people. Let’s go all in on that.” So I think partially it’s simplifying, but I also really just believe in more authenticity and vulnerability. I think that as a culture we’re headed more towards that. I think the girls of the younger generation, just to talk on the beauty side, are more excited about models that haven’t been retouched, and different sized women on the runway, and I think we’re getting away from some of the perfectionism of the perfectly curated Instagram and sort of living through that vicariously.

I don’t feel like there was a lot of people when I started out talking about how hard it is, how many tears there are, how alone you feel. I posted on Instagram the other day asking people to share their things and the number of people that said, “I feel so isolated and alone.” Which wasn’t my experience, I love being by myself for eight hours, I just get in the zone, but it was so prevalent that I realized, “Oh, that’s a thing. Huh, who needs to help those people? I don’t know if it’s me, but what do we need to do to make those people feel less alone?”

I think that is so challenging and people talk about it less than other challenging things like parenting or death of a parent, or cancer. There’s things that we know we need to get together and have a support group. We need to have forums. And of course, we do have some of that, but I find that through my being so honest, we’ve built such a strong community through Instagram of people just saying, we have so many comments of someone that says, “I’m in tears reading this. This was exactly what I needed.”

And I wasn’t going on to try to create that emotion, I was just sharing, “I’m feeling overwhelmed today,” or “These things are going wrong behind the scenes.” And I think people see so much beauty and perfection that is making them feel like, “I’m so far from that.” So I think the more honest we can be, as you just said, like you hear me say, “Simplify,” and your honest response is, “That sounds hard.” Rather than being, “Oh, yeah, we did that years ago. Everybody should do that.”

So I think really sharing, this is a challenging thing. If it was easy, then not only would everyone be doing it, but everyone would be succeeding. But the stats are still that 50% of businesses fail after five years and that’s been a pretty solid trajectory since the ’90s, and so it isn’t a slam dunk. But of course, we also don’t want to be be Debbie Downers, so you don’t want to just be talking about how hard your life is, so I think you really have to find that balance and being encouraging, optimistic, inspiring, really supporting people in their dreams and not being a nay-sayer.

But then also, being like, “Listen, I’m not going to sugarcoat it, there’s a lot of crying.” There’s a lot of crying, it was hard, I get it. And I don’t have all the answers. I can know some things, but I have no idea how to make it a cake walk for someone starting again. Maybe somebody has that answer, but I don’t. I say it’s like being a single parent of triplets. It’s just going to be crazy for a while. I don’t know that there’s a way to do that, unless you can afford three au pairs from day one, which is no one.

LR: Most can’t, yeah. Well, Hilary, it’s been an absolute pleasure.

HR: Thank you so much.

LR: Thank you so much for being here.

Hilary Rushford: This was great, I so appreciate it.

LR: Yes, absolutely, will you sign our wall?

HR: Yes.

LR: It’s right behind you.

HR: Oh, I was like, “This perfectly beautiful wall?”

LR: You’re like “Which wall?”


Want more Modern Ontrapreneur Podcast?

Check out the previous episode featuring Alejandro Rioja of Flux Ventures.


About Ben Cogburn
As Ontraport’s Traffic Manager, Ben Cogburn spends most of his time in our parking lot. Just kidding, he’s our resident digital advertising guru. As a geology enthusiast, Ben graduated from the University of California, Santa Barbara with a degree in Environmental Studies. So to say that he likes rocks is an understatement. You can find Ben hanging out with his rock collection, playing video games or hunting down new figurines to add to the impressive display he has on his desk.