Mastering The Shift From Chaos To Clarity, with Sasha Tripp
July 09, 2025
Hosted By
What separates entrepreneurs who collapse under pressure from those who come back stronger? Sasha Tripp—a real estate entrepreneur who survived financial disaster, market crashes, and personal crises—shares how she transformed adversity into her greatest breakthrough. Discover the mindset shifts that helped her lead with resilience and rebuild her business, and how Strategic Coach® gave her the tools to turn chaos into clarity.
Here’s some of what you’ll learn in this episode:
- What made Sasha realize that she had to either improve her skill set or get into sales.
- Why the sky’s the limit in real estate if you have the right work ethic.
- Why Sasha thinks she might never be employable again.
- How Sasha’s entrepreneurial path and her Strategic Coach journey have always overlapped.
- The hardest thing Sasha has ever had to go through.
Show Notes:
True entrepreneurship is tested in the valleys, not just the peaks.
You can’t tell if someone's a really great entrepreneur in the best of times because they have a lot of supports in place.
The 4 C’s Formula®—Commitment, Courage, Capability, and Confidence—is the foundation of overcoming any challenge.
It requires courage and commitment to gain new capabilities and confidence.
Confidence feels good. Courage feels lousy.
If there are going to be problems in the marketplace, residential real estate is where it shows up first.
When everything falls apart, your mindset determines whether you rebuild or retreat.
Entrepreneurship isn’t about avoiding risk; it’s about managing fear while moving forward.
Entrepreneurs have the freedom to pivot and change when it makes the most sense to do so.
If you don’t have the answer yet, it might be that you haven’t thought of the right question.
Strategic Coach isn’t about tactics; it’s about training yourself to ask better questions.
Strategic Coach is a community of unbiased people you can talk to about your challenges.
You can want what you want. You don’t have to justify it.
Your business should fit your life, not the other way around.
The fastest way to grow isn’t working harder, it’s thinking differently.
Resources:
The 4 C’s Formula by Dan Sullivan
10x Is Easier Than 2x by Dan Sullivan with Dr. Benjamin Hardy
Who Not How by Dan Sullivan with Dr. Benjamin Hardy
The Gap And The Gain by Dan Sullivan with Dr. Benjamin Hardy
Episode Transcript
Dan Sullivan: Hi, this is Dan Sullivan. I'd like to welcome you to the Multiplier Mindset Podcast. Hi, everybody, it's Dan Sullivan, and this is the new episode, our latest episode of Multiplier Mindset. Such a terrific treat for me to sort of give some commentary on a wonderful entrepreneurial story, and this is by Sasha Tripp, and Sasha is from Charlottesville, Virginia. I met her right when she came into the Program. Of course, she was in my workshop for the first year and she just struck me as a totally positive person right from the beginning. But she tells a story of what she recounted on our interview was really tough times for an entrepreneur. And all the different aspects she's talking about, how do I survive this? They had tremendous loans and that that they were carrying and everything else.
And what I love most about Sasha's story is that she took full responsibility for the project. She took complete responsibility for the business. She had team members that she had to support, and her incredible emotional and intellectual strength of just saying, I'm totally committed to making this work. I don't care what it takes. You know, I've been coaching entrepreneurs for 51 years, and we've been through some tough times. I mean, there's been ups and downs in the marketplace, and usually real estate is the first thing, residential real estate, is the canary in the coal mine. You know, if there's going to be problems, the residential real estate is really going to be the place where it shows up first.
One of the main concepts in Strategic Coach, and it's becoming more and more apparent how important this concept is, it's called The 4 C’s. And that for an entrepreneur to meet a challenge, number one, you gotta be 100% committed that you're going to do it before you have the capabilities to do it. You have to be committed first, okay? You don't have the capability yet, but you're totally committed. You don't have the confidence yet, but you're totally committed. And then what that requires is just a great deal of courage. You just have to stick with it and move forward and you have to be courageous.
And people often ask me, well, what's the difference between confidence and courage? And I said, confidence feels really good. Courage feels really lousy. And I got to believe that there's something miraculous that goes on, that when you're committed and you're courageous, it's the commitment and the courage that actually creates the capability. And when you get the capability, it's unique to you. No one else in the world has this capability, because the building ingredients was your commitment and your courage, and it's unique for every individual. Then you get confidence as a payoff, and you could tell that Sasha's now in the confidence payoff that she got for going through.
And this was a multi-year experience. This wasn't something that happened in a week or three months or anything. This was going on for a long period of time, you know, 2020, ‘21, ‘22. And they were still in the midst of that. And I always tell people, you don't know whether someone's a really great entrepreneur in the best of times, because there's a lot of things that are supporting you. But when things are really tough, and I can't imagine a situation as tough as the one that she found out about, because it wasn't just her own individual pulling something off. She had to rebound from a bankruptcy. She had to deal with the fact that houses weren't really, really moving all that well during the COVID period. You know, you couldn't do in-person meetings and everything like that.
I just admire Sasha so much, and I am so grateful that we were able to capture her recounting of this story, because Sasha says, well, you know, this is what happened, and I went through it, and I came out the other side. But I think anyone has to just sit back and say, wow, this is really what entrepreneurism can be about at certain points in your life. It's not all mountain peaks. There's some really deep valleys that you have to go through. So I want millions of people to see Sasha's story.
Sasha Tripp: I am Sasha Tripp and I own Story House Real Estate, which is a residential real estate firm in Charlottesville, Virginia. And then I also do coaching, public speaking, and training of primarily real estate agents, but real estate agents, mortgage brokers, and small business owners across the nation. And I've been at Strategic Coach I think a little over five years. I'm kind of a digital hoarder. And so I was looking back through all my notes. And my first set of notes was from 2019. So a little over five, very wild and very crazy years. And so much happens in five years, which is really that it seemed like it had to have been longer because my life is completely different. But yeah, just five quick years of growth and expanding my mind.
I was a religious studies major at the University of Virginia, and I came out from school, I graduated in 2005, and we were kind of going into a little bit of a market recession, and I had no marketable skills as a religious studies major, as it turns out. I was very well-read, and I stayed in Charlottesville, Virginia, which is where the University of Virginia is, and I looked around me, and everyone's so educated here. Everybody had advanced degrees. A lot of doctors, a lot of attorneys, a lot of high paying, very high, you know, intelligent roles here. And I realized that with just a Bachelor of Arts in Religious Studies, I wasn't going to be able to make a living living in this town and stay here unless I either up my skill set or I went into sales.
And so what I realized was, okay, I've got to find my way into the sales industry. Real estate has a really low barrier of entry. And so I was licensed and I had a job the next day and everybody's like really excited. I'm like, oh God, got my first job, but has no criteria. And then it was the worst real estate couple of years, real estate recession. And I spent a ton of time educating myself in that time. I wanted to buy a house. I felt like I didn't know anything about home ownership or budgeting or economics or really anything that would be useful life skills. And I wanted to take the real estate class because I just didn't want to make an uninformed decision.
And it just sort of blew up from there. I got my license and I was like, well, I might as well hang it at a brokerage and then it just kind of kept coming and I realized for the level of work ethic that I had, that the sky was the limit in real estate and I really enjoyed working for myself and feeling like I could maneuver the way I felt was right for a business that would work for me. So as soon as I got a taste of it and learned how to survive, which took a couple of years, I just never looked back and now I kind of joke, I don't know if I'm employable ever again because I just have such ideas and I want to move on them very quickly and it's just so fun having control over them and figuring out how to kind of build it into your life.
So I've been in real estate almost 20 years, but my firm, I opened my company, we're on our sixth year anniversary. So I had been a entrepreneur for a year or maybe six months before joining Strategic Coach. And it was a really nice run for a couple of years. COVID was crazy. And that actually kind of goes back to tying into Strategic Coach. I was in the Signature Program. And I remember when I joined, it was marginal that I was able to join. I didn't know if I could afford it, but I also didn't know if I could afford not to do it. And I joined and immediately it was like, oh, it's going to be Dan's last year teaching 10x. And I was like, okay, well, you know, you're having heart palpitations. And it's like, well, I feel like I'm supposed to be here.
So I immediately leveled up into 10x, knowing that I wanted to spend time with Dan, and then COVID happened, or I mean, it was all around the same time. It was the biggest blessing of my life because being able to jump on all of those webinars and jump in and out of any session I wanted while I was in a little bit of COVID paralysis for a brief period of time trying to figure out how to sell houses without leaving our houses, it was literally life-changing. So I probably got 20 year’s worth of content from Strategic Coach just in that one year. So my path as an entrepreneur and my path at Strategic Coach have overlapped and been moving together basically since the very beginning, which is kind of cool.
You know, I'm a faithful person, I really do believe that like, things come to you when they're supposed to be. And you know, Dan says it a little better that like, you find what your mind is looking for. He says it a much more attractive way than that. But it's really interesting. I do get an idea. I feel faithful about it. I feel committed to it, which you learn a lot about how that kind of creates the circle itself. And then all of a sudden, like synchronicity happens, or magic happens, or the 4 C's happen, whatever you want to believe is the reason. And the world just sort of seems to start putting the path in front of me, which is kind of neat. It's the fun part of being an entrepreneur, because then I can sort of pivot and change when it makes the most sense to do that.
Which one of the six years do we want to talk about? But yeah, there was a really pivotal moment that it was the hardest thing I've experienced in my life. And I would say I've had some adversity in my life. I've gone through a very contentious divorce. My sister passed away unexpectedly just this past year. My dad had his leg amputated. He had a pretty bad illness and we had to kind of get him transitioned very, very quickly. I had skin cancer scares. I've had a lot of adversity in my life. There was like a path. I could see a path.
The thing that was really pivotal for me was a home build, I would call disaster that we went through. I'm a residential real estate agent. I know how to build a home. I know how to select who to build a home with. I had worked with a home builder. I was the marketing rep for that home builder for five years. So it's not like I didn't do my due diligence. He was an amazing builder. And he went bankrupt in the middle of our home build. And to say that it was scary and paralyzing is the biggest understatement ever. There was a 30-day window of time when we had $700,000 of liens show up against the property for things that we had paid for, but the vendors hadn't been paid for.
And working through that was, you know, COVID was tough, adjusting during COVID, but working through that process was the most pivotal. I think it was the time that Strategic Coach really played a major role in my life and my decision making and my thinking and how I got around a problem like that and was the hardest, by far the hardest part of my entrepreneurship, despite the fact that it wasn't specifically tied to business. Cash flow is very intimately tied to business, though, so it was very painful. Confidence. It's the most crazy unbelievable story ever.
Our house, the cost of it was twice the cost and I remember when we were not like major spenders the original cost felt really scary. And then twice the cost is really shocking. We had to dynamite our property. We became general contractors. It ended up being a 10,000 square foot house, which is not what we signed up for. We don't need a 10,000 square foot house. It took three and a half years of our life. But confidence, going into that and knowing like, I'm going to figure it out. I committed to the fact that we're going to figure it out. And I decided, let go and let God. I don't know where people will be on the faith spectrum, but I had to make a decision that I was committed to that. And if I was meant to be homeless and tell my story and tell my testimony and share that and write a book about how I overcame that as a residential real estate agent, you know, I kind of just decided this is what was supposed to happen.
So I committed to finishing that build and doing what we had to do to get through that build and learning the skills that we were going to have to learn to get through it. We got through it, but I think between confidence and knowing I had the right Who's, or I could find the right Who's, and knowing that I had relationships in this community surrounding me that I could go ask the questions to, but then also for me, energy. Having a place to replenish my energy was massive. I'm so scared I'm going to do this podcast and it's going to seem like a creepy sales pitch for Strategic Coach and you're not going to use it for anything. But they're so aligned.
Before Strategic Coach, I would probably get stuck a little bit more in a bad day. I would kind of mull over adversity a little longer. I'd get paralyzed. I'd kind of pout and get beat down a little longer. And going in with the mindset of like, the obstacle is the way like we can overcome it. We have the right tools We have the right community and really it's just a matter of thinking, like, if I don't have the answer yet, it's because I haven't thought of the right question or I haven't worked through the right question. It's hard to describe what my life would be like without those things, but that just happened to be the one instance where we were able to get through something that I don't think a lot.
Meanwhile, like, we had our best year in business ever. I had a one-year-old child and we got through it. I don't think I would have gotten through it. And I honestly think if I hadn't been an entrepreneur, with the problem-solving mentality and like, the buck stops with me mentality, it would have been a lot harder. It might have paralyzed us, it might have knocked us out. Like I don't know that everybody would have gotten through that process. So yeah, being an entrepreneur gives you this like, I don't know, incredible tool bag of things that you wish you didn't have to pull out so often, but it feels like it's more and more useful by the day right now. It feels like we're using and calling on those things all the time.
So long story short. Oh my gosh, most afraid of, it's like, if I don't get like a bulleted list that I could use—cash flow, destroying our family's livelihood. You know, I'd worked really hard to build up safety and security and freedom, destroying that. But also there was this ego part of me, this pride, like, how am I going to be a successful residential real estate agent when I've walked myself into literally the worst home building disaster. How will anybody trust me? So again, not a salesman for Strategic Coach, but having the community of unbiased people that I could have in confidence and I could go and talk to about this stuff because I was terrified of my reputation and what it would look like in the market.
Yeah, I was terrified of a lot of things, going bankrupt, foreclosing on the house, you know, there were days I felt like there was such a bad omen and cloud and I'm not like a cloud feeling person, but I was scared to bring my one-year-old in the new construction house because there was so much anxiety and panic. I was like, is he just gonna go tumbling out like a window that's not built in yet? It consumed us. I was scared our marriage wasn't going to make it through. My husband and I learning how to be general contractors on a 10,000 square foot property, you know, that wasn't the most fun part of our marriage. So I was scared of everything.
The outcomes today are like, I have an amazing testimony. I'm still scared sometimes. Like I look at it, I'm like, I still don't need a 10,000 square foot house. Like every day we're debating, like, what was this here for? Am I supposed to foster like 25 kids? Am I supposed to sell it? Like, what am I supposed to be doing with this house? But my business is better, my testimony is better, I became a better leader. I think I was able to lead people through. I'm not gonna trivialize or make any comparison between adversities. Everybody's adversity is an adversity to them and is major to them. But I think in that time, I was able to lead by example and really show my team what it could look like to come back to Positive Focus, to come back, you know, Gap versus Gain, come back to like, okay, what are the incremental wins in these seasons that don't feel as winning?
And then I'm able to control my energy, which is the biggest thing. I remember I went into a session one time, and a friend that I had had in the session, I was beat down. I felt like we were just getting crushed from every angle. And a person that I'd only met a couple times before just walked up, and I don't know if I was just wearing it that day or what, but he just said, how's your energy today coming into this, Sasha? And I was like, oh, it's really bad. I'm really glad you asked. And by the end of being there for two days, I came back out and it was bad in that moment, but I am fired up. I come out of it so driven, so ready to go. And so it's taught me that I ultimately control that and then it bleeds into my team and my team feeds off of it. And if I can have my energy thrive, in general, the team around me is going to be able to do the same, which is a crazy power, like what a superpower to have in general.
So yeah, those are some of the lessons, but there were many and the fears don't ever go away when you're in, you know, anybody can have a really neat house that's two times what anybody can like it. It doesn't mean that they're going to be comfortable in it. So that chapter will close soon and we'll figure out the end of it. But the other thing Strategic Coach entrepreneurship showed me was, I've always wanted to write a book. I always felt like I had to tell my team why. I had to answer why or why this season was the right season or why I was going to take time away from my business to do this thing. And I feel like between entrepreneurship and Strategic Coach and a community of people that have that same mentality, I realized like, I can just want what I want. I don't have to justify it. And that is okay.
And for me, I look at so many of these things now as it's a big story and it will be for good. I'm not sure I've found the extent of the good yet. I haven't peeled all that away, but it will be for good. And what a cool way to look at adversity and struggle. So it's truly a gift. I feel like I have to tell you what the differences are in five years. I can't, you know, attribute them all to a Strategic Coach, but five years ago, I was still getting out of a very ugly divorce. I was single. I wanted a child, but I was going through infertility. I had a brand-new company and we didn't even know if it would last because we were tiny, tiny, tiny, tiny. It's very scary to be up against these bigger competitors.
So five years later, you know, I found the love of my life, got engaged, got married, got pregnant, built a baby, had a baby. I now have all of these things. I have an almost four-year-old, so I guess it's probably five and a half years. I have a business that's thriving. I built my dream home for better or worse. I have truly a dream home. And it's like my whole life is so different. I think Strategic Coach probably had major, major impact on all of it except for my divorce because that was very far down the line by the time I had joined. But it may have even given me some momentum after that because after my divorce I was hiding. I felt isolated. My husband and I had been together for a long time. We only had adult friends We had a lot of couple friends. I was hiding and I think the biggest change for me is that I don't feel like I have to play small anymore.
I think I was always just playing a little smaller and making myself a little less when I was in rooms locally. And then when I got into Strategic Coach, it gave me permission to just show up unapologetically, have the things that I want to go after and then kind of create the life that I'm looking for. And you don't feel that way after a divorce. You feel like a shell of yourself and like everyone's judging you. It's very isolating and scary. So it's been an incredible five year path. But I also just feel like I'm free to just go be me. And I know what that looks like now. And it's not dictated by what other people kind of expect it to look like. And now it's really fun just going to every session thinking about, okay, how can I get closer and closer to it? And you know, it evolves.
So there's always work to be done. But again, I don't focus on the Gap of the work. It's really on like, how incredible that path has been, if that makes sense. But yeah, it's really fun. And now we're doing a major business model change. I found my 10x. I used to look at real estate and I was like, I do not want to 10x this. If I had to work with 10 times as many clients, I would just poke my eyes out. It's so hard to keep up. It's a lot of emotion. It's a lot of people. And I just kept thinking like, okay, what is 10x? I'm going to have to have satellite offices. That sounds exhausting. I found my partnership and I found my way to 10x in a way that I'm really excited about. And it's just, you know, how fast can I go and how much energy can I maintain through it?
So it's going to be an exciting next five years. If you want to go faster and further, I would just do it as soon as possible. For me, when I talk to people, it's like I meet people in businesses and I'm like, oh gosh, you should join Strategic Coach. I just can see it. It's like oozing out of them. And when I talk to them, I talk to them about the community of people that's like a safe community where you can go and be fully yourself. Whereas I think a lot of big business people in smaller communities or in a certain board of directors they're on or a certain committee they're involved in or a certain business that they have a smaller partnership role in, they aren't fully themselves. They're sort of a slightly lesser version of themselves because they don't want to be too much.
So you have this community where you just show up. And if I'm being totally candid, I was used to coaching where you'd show up and it was tactics. It was like, okay, you're a real estate agent. Take this list. This is how you get a house to contract to close. This is the email drip campaign you send. And so my first two sessions in Strategic Coach, I was like, I just paid a lot of money to just think, like to just think and fill out worksheets. And I was so, it's so funny how narrow your mind can be. And I was just like, this is crazy. I'm not even being told what to go do. And that's the beauty of the Program is like, you have all the things you need to go do and we're probably stifling some of that by doing these pre-prescribed lists of things that other people have done before us that cater well to their desires and their business.
So I always say it's the place to go to train yourself to ask better questions or seek out better advice to get you to the answer that is right for you. Whereas most of our life, at least mine, had been spent in communities of people that were sort of prescribing a path that led people to success before you. So I would not be the same entrepreneur. I don't even know if I would be an entrepreneur if it hadn't been for Coach because there were some days that I needed that energy boost. But it is truly life-changing because, yeah, I'm a better mom. I'm a better spouse. I'm a better leader. I'm better in the community. And for me, 10x was not about revenue. That would be really cool, especially after the financial setback that we have just had. I'm open to 10X-ing revenue.
But for me, it was 10x impact. I'd rather train 10 of my agents to go sell a few houses each than sell 10 houses myself, even though the financial impact of me selling 10 houses would likely be greater. So for me, it was impact, and I just feel like I don't think I would have gotten there. It would have taken me a lot longer to get there on my own, scratching and clawing. So the community is amazing. I can't say enough good things about it, but it really is for someone that wants to build a business around them. If it's an entrepreneur that's sort of looking to just sort of stick with what they've been doing and kind of ride that out into the sunset, I don't know if it's the best community, but I think most of us with that like entrepreneur blood want to find a way to do it that suits us, that keeps us excited every day.
And I've never found anything remotely comparable to this community for that. For the audience of who would be listening to this, I think it's important to know that all of the coaches are amazing. My coach, Chad Johnson, he's just an unbelievable person. He has this incredible marriage. He has this incredible faith. He's so fit. I remember when I first met him, I was like, surely this guy is not always this happy and upbeat and positive. I've seen him through a lot of things now for five plus years and some bad moments in his life and he is the real deal. The coaches are so impressive and that for an entrepreneur, if you think of it grand scale, it's like, you know, you've got the Dan Sullivan running an organization and then you have all of these people, but most of these other coaching programs and systems in the world do not survive without Dan, you know, like without, you at the top.
And so what I have found is it shows this path of a way all these entrepreneurs struggle with, what's the transition plan? What's the succession? How do you ever leave this and not just like, destroy your legacy and leave your people behind with nothing? Strategic Coach is this perfect model that shows you how you can replace yourself in a way that's full of integrity, full of life. And that actually fuels you more than you doing the thing that you loved for so long that you built that was like your baby. And so that's been the coolest thing for me because I'm starting to think a lot about my own replacement and how I could feel good about that. And it takes a lot of ego and pride out of the way to see like, if Dan can replace himself with something that people will be happy to be trained and coached by, you know, I think the standard, the bar is a lot less for me and my much smaller business.
So it feels very relatable. It feels very doable. And it's like there is a path there. You just have to ask the right questions and talk to the right people to figure out what makes it work for you. So I love thinking about that. And I think it's really important because you don't have to be sitting one-on-one with Dan Sullivan, you know, for it to be super impactful. I would say that like every small aspect of the Program is extremely impactful and you can't say enough of it. It's hard to really understand it until you get in the room and you experience it.
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