Practicing Generative Listening And Micro Pivots To Raise Your Game With Rache Brand

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Live Your Possible | Rache Brand | Generative Listening

Feeling unfulfilled despite achieving external goals? Many of us follow paths shaped by others’ expectations, neglecting our own unique aspirations. Today, our guest Rache Brand talks about generative listening and offers a roadmap to break free from autopilot, discover your true north, and conquer the challenges that hold the key to your personal definition of success. Rache is the co-founder of Superstruct, a company that makes your great ideas flourish into thriving businesses. Tune in and join us on a journey of self-discovery. Break free from expectations and chart your own course to conquer the challenges that truly matter to you.

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Practicing Generative Listening And Micro Pivots To Raise Your Game With Rache Brand

You’re going to find some personal epiphanies as we speak to Rache Brand. She’s an active founder, an operator, and a builder. Her journey is windy, but aren’t they all? In 2022, she transitioned into private credit, and this has been the most rewarding part of her journey to date. She joined Spring Hollis in her private credit fund, Star Strong Capital, and together, they built an advisory practice to help businesses stay in the market and grow for the long term.

Rache believes in a positive sum mindset working in the same direction towards growth. She also dives deep into her windy journey and how she has grown from tough moments to embrace the happier ones and has come out stronger to live with greater intention and a clear purpose. She shares a variety of techniques, practicing generative listening and leveraging micro-pivots as a way to go forward with what is showing up. This is allowing Rache to focus on what is most relevant to achieving aspirational dreams and goals. Rache even offers up her availability in some tools to help guide founders to influence raising revenue in place of capital on the path to achieving sustainable success. Enjoy the show.

Live Your Possible | Rache Brand | Generative Listening

Welcome, Rache Brand to the show. How are you doing?

I’m great. Thanks so much for having me.

It’s great to see you again. I was at your Sip Session a couple of months ago with Fathom. You did a fabulous job.

Thank you. It was so much fun and I enjoyed having you there. It was great.

That was cool. We covered so much ground and I feel like we’re going to do that as well. Let’s jump right in.

Let’s do it.

Tell me, what are you passionate about these days? What are you focused on with your energy?

Interestingly enough, it started when I did a Sip Session in December with Generative Listening with Brent, but I am actively listening to myself for the first time. It’s something that I’m doing on the business side but also, it’s leveraging my person and all the things I have going on my own life that seemed to be connected to the work that I’m doing.

What conversation? How does that work?

Generative Listening

Interesting that you asked that because I know you know a little bit about generative listening. I feel like it’s a baseline. We all have never learned how to listen thoughtfully and this idea of generating a conversation and without having a direction, without having a preconceived notion of what the end result is going to be.

I did that with myself and I realized why my ability to lead and be the best person I could be was not being fulfilled. I pulled back. I spent a lot of time and energy listening to the things that do make me tick that are my unique areas of focus, my special attributes. I did a human design workshop, which was fascinating with a company called Aero Society. I learned all about the way that I work and that led me to realize that I was feeling weighted in aspects of my life, my marriage, and my relationship with my children in the place that I live in living in Simsbury, and also my work. I’ve made some active changes.

It’s a balanced look, too. I like how you covered all the elements. If you think about the wheel of life, you covered it there. How did you create the space to listen? We’re so busy. How did you create the space?

I don’t sleep anymore. I’m tired all the time. Other things have gone out of the window as a result of it, but in order to make a catalytic change and to get from one place to the next. You have to dig in. You can’t live in the landscape of gray. For me, it was uncovering and looking at every single aspect of my life and starting from that point and moving forward. That’s where I am now. I’m in the execution side of it and I keep micro-pivoting as I go because there are lots of changes that need to come. It’s making a decision to be extremely active in the process.

To spark a catalytic change and reach your next destination, you have to dig in. You can't just live in the landscape of gray. You have to uncover and look at every single aspect of your life, start from that point, and move forward. Share on X

That’s good. Are you building pauses throughout your day? You get a routine to make sure you reflect on what’s showing up or what you’re hearing, which is helping you shape what you do next.

It’s such a good idea. I should do that. I would say it’s a little bit less prescribed. One of the things I did learn about myself is that I’m not great at routine. The second I start having a routine, it takes me down in a different way. I try to honor that and go with the flow in terms of what my kids need on different days. Every day of the week is a different day. Also, my work schedule ebbs and flows from a travel standpoint. That makes it hard. I also have an apartment in Manhattan. Depending on when I’m there, that’s a different lifestyle that I live also. It’s something that I’m working toward.

It sounds like you’re building this within your day. All of a sudden, something pops up. You don’t ignore it and do what you’re doing. It sounds like you’re slowing down to notice it and do something with it.

I’m going towards it. It’s such a weird feeling because it feels so uncomfortable all the time. I’m like, “I feel something. Pause. I have to understand why I feel this way,” then actively pursuing it. A lot of times, we brush it aside and we cover it over then years go by and we don’t deal with it. That’s why we have such a huge mental health crisis. We’re not listening to the things at the moment. I’m trying to do better at that because it’s not been a great five years.

If you hear multiple things or maybe you see 4 or 5 different ideas pop up, all of a sudden, you have these tabs. You got to open up. How do go through that?

The one that is the hardest. I work my way down. I figured that one. If I can get through it, then the other ones will be easier.

I love that. I used to work with different teams that would always work on the easy pile then the hard stuff would never happen. Those are the biggest issues that would follow. Is that the same way you’re thinking about it?

I can easily distract myself and send a hundred emails because they’re in my inbox, but some of this came from giving me the permission to say, “That’s not necessary at this moment. It’s not going to be something that is generative in a way that makes sense for our business. Let’s pause on that.” That’s nice to have and not necessary. Focus on the necessary things you need to do first that are going to move the needle.

Focus on the necessary things you need to do first that will actually move the needle. Share on X

I love that reference to generative too. You picked one of the hard ones and you mentioned there’s the last five years have been tough. Are there certain areas that you’ve had to get through, learned from, and come out stronger?

Working on stronger. I certainly know that I have no limitations to what’s possible. I can keep the glass ceiling keeps breaking through. A quick reference, in 2019, my family and I moved from Guatemala, which was an extremely easy and beautiful lifestyle that we had chosen. That we had intentionally chosen to be in with our children. We had moved there. We went on a vacation in 2014 and never went back home to New York.

It made a lot of sense for us at the time. I had my son there and my daughter was one when we moved there then we lived in the 1%. It was an incredible life. We had all the support that we needed. We had an amazing home. We had great friends. We had everything but we knew that it wasn’t a forever moment. I wasn’t growing at the rate that I had expected to or hoped to in my life. I wasn’t being challenged in the same ways.

I had an opportunity with my job two years prior to working out of San Francisco. I was commuting quite a bit. I also had a job that I had taken on in Las Vegas. I was never home and it felt like I was traveling a lot. We moved on December 15th of 2019 to San Francisco to change our life, to put our kids in private school, in an inner-city private school, nonetheless, Montessori and a bilingual neighborhood. We lived downtown.

I had a partnership with the Venture Capital Fund and that was December 15th of 2019. We all know what happened in January of 2020. Our container hadn’t arrived before the world started shutting down in San Francisco and that became the hardest year of my life of bouncing around multiple places. We’d pre-paid for everything in San Francisco.

It was hard to lose all that but our focus was on getting ourselves back to a place where we felt centered and that was Connecticut. We found Connecticut on a Google search and we rebuilt our life. I left my partnership, changed careers, and tried to make a community for myself here. I feel now, four years in, we have a decent and interesting approach to life. It’s very different than what I had in Guatemala.

It sounds very different, especially when you think about Guatemala then Connecticut. Welcome home here. I’m also in the great State of Connecticut. As I said, we’ve seen each other at these Sip Session events with Brent Robertson and others. I’d love to hear about how this is translated into the work you’re doing. I know you have a passion for food, and helping people to start up businesses and be very successful. I know you have strong interest in women and investing in investments. I’d love to hear wherever you’d like to go.

Rache’s Story

That’d be great. I’m not going to share my whole story but the notes that are important. I’ve been in the food industry since I was basically born. I always had a question or interest in it. I worked as the drive-thru girl at McDonald’s when I was fourteen. I worked all through high school to college, working for various food companies like Compass Group.

I ended up taking over my family business and making that into a food and sustainability platform. I grew that until 2012 and exited from there. I had three spin-off companies. I would not say it was a big exit but it stimulated and helped me to understand some of the things that I need to do to help other companies and founders do things differently than I did. I went and worked and did a research project with Cornell in the Food and Brand Lab, a very large research project with City Harvest in Manhattan with bodegas.

I also worked alongside the K-12 platform. We did all of New York City’s public schools. It was 1,200 schools. A pretty impressive research project. It was all with plate waste, which if you can imagine. That was interesting to learn. What it led me to ultimately was Chobani, which was super pivotal. I was in this opportunity around operations but also watching things that people weren’t understanding about a new and disruptive product like Greek yogurt and making changes as a result of psychometrics and preferences.

That helped me to understand a lot about the world which led me into venture capital because I was interested in helping to continue that passion around the change of food and technology. I’m like, “If we’re not getting there on the CPG side, I know that we can get there from finance.” Finance is top-down. We’re driving change.

What I found in venture capital and part of my big change over the years was leaving an industry that I had so much hope for and realized was never going to get the job done. I landed in private credit thinking that the better approach was writing loans and helping these to be more sustainable companies to keep the change and market longer and not lose these great ideas. Now I realize that without the advisory service, which is what I started my business with in 2000. You aren’t going to get there.

Superstruct is where I’ve landed. I have a 2030 goal, which I’ll share in a moment but I want to share a little bit about Superstruct if that’s okay. It’s been wonderful to be a part of this community because I also feel like I have great supporters and people like you who are willing to listen and help me shape this. This is something I’m building in real-time. I don’t have all the answers. I don’t know if this is the perfect way forward but what I do know is that businesses have been building unsustainably for a very long time.

They’ve been doing that because access to capital was available and opportunities seemed like the only way to grow was to build the market by buying the market. What we’ve found over the last couple of years is that’s not true. All these great ideas that fell into the market in 2000 and beyond, they’ve been hurrying up to figure out a way to sustain them. That sustaining mechanism has been capital and the capital drying up puts them at a bad disadvantage because the market doesn’t want them.

They’re not ready for it yet. The disruptive ideas to new and novel. They have not iterated enough with their customer. They haven’t figured out their sales strategy. They don’t know their ICP or their customer profile that’s important. All of those components have gotten to a place where we have lost a lot of early-stage companies. I have a huge problem with the fact that most people from an equity standpoint, want to be in the growth stage middle market.

If we don’t have these businesses here building and growing in a sustainable fashion, we’re never going to get to that growth stage. The change I want to make in my lifetime is exponential. The only way to get there is to make sure that these amazing brilliant ideas stay in market. They fulfill their goal and their goal is to create the change that’s needed. That’s what I’m doing. I’m super shocked and I feel amazing with it. It’s a pretty simple tool.

To achieve exponential change within our lifetimes, we need to make sure that these amazing ideas stay in the market and fulfill their goal. Share on X

It’s a four-hour session and we’re flipping the concept of business growth on its head. It’s not a 90-day session. It’s not an execution strategy. It is three next steps. Once you do those three next steps, let’s do three more. Let’s keep notching forward and as I have with my life, with my learned experience around micro-pivoting, I’m doing the exact same things with the businesses I serve. Keep pivoting forward and keep tweaking it along the way.

Keep iterating. It sounds like you’re saying, all of a sudden, you tackle what’s in front of us rather than overreach it and overstep. It sounds like taking those iterative steps to make the big happen, to change the way we think, the way we do, and the way we are. The way we want to be present to what’s happening within the work, what we’re doing, and the impacts we want to make.

We have nothing left on the table.

You said you have some huge aspirations. I don’t think I heard that. What does that look like? Maybe that’s the 2030 goal. Maybe that’s something bigger with the companies that you’re working with.

I believe in the intersection between food, healthcare, and lifestyle and we’re making ourselves sick. The model is that we have commodities that have helped us to build business. Commodities like oils, sugar, sugar, wheat, and soy have created things like the Krispy Kreme Donut and other wonderful dopamine-driving products, which have then made us happy for a moment and ultimately sad later. We’ve created Type-2 diabetes.

Both of those create monetization events for companies that are paying taxes, which is great but those companies ultimately then stimulate new solutions like big pharma, which can’t pay all their bills because it’s impossible to support the entire health care crisis that we have around type-2 diabetes. Guess who picks up the tab on the other side? The government.

We have an unsustainable system. We know this. The project that I want to build is called the Whole Human Project, where we think about it differently. We spin up different businesses to support it. This is a new type of capital that doesn’t exist. It would be a hybrid. I’ll call it dequity for the moment, but I’m not sure what it looks like. It would be leveraging the concept of debt or loans with a hybrid solution that enables them when they’re struggling to have a little extra time.

It is similar to a convertible note or potentially like a small family office that’s doing a project finance opportunity but it’s a little bit bigger than that in the sense that you’re a part of the fund and part of the network. What we’re building with Superstruct, the idea is that it’s advising on that. I have to make this successful. I have to make Star Strong Capital and our $500 million fund to raise successful in order to prove that I can raise the capital.

I have to ensure that I have the ability to deploy it in healthy companies. The only way we get there is by having amazing advisory customers who have run through the program and we know are healthy and that comes back to Star Strong Capital. They can be across all disciplines of life. The goal is for us to build a diversified set of healthy companies and that proves the model that this works. As we start to segment it out into different groups and different industries, we can test it in those theories. Now, it’s more about that broad-stroke generalist approach and being able to ensure that we can do this.

The Human Project

What type of companies are you working with to come back to the whole human project?

On the whole human project, it would be related to everything from new agricultural and new farming techniques to new CPG, new grocery chains, and platforms around food. On the healthcare side, it’s more food as medicine approaches with more of an emergency-style platform. You don’t need a lot of the things that we have if we are supplementing correctly and have the emergency services on the other side when it doesn’t work. On the lifestyle, it’s approaching work-life balance better.

It’s ensuring that we understand our bodies and our human design. We know the approach that we’re taking. It needs to be done in a way that’s specific to us and we’re all snowflakes. There is a different version of us out there that no other person connects to. We might connect on lots of different points, but you have to be building your life according to you and what your unique needs are.

You have to build your life according to your unique needs. Share on X

We truly are all unique. I love your point about the whole genre of thinking, too. We have to be listening and how you started the show, with connecting to who we are.

That’s right. Thanks to you and Brent. I’m getting someplace with my generative listening.

What Healthy Businesses Look Like

It’s fascinating. You’re bringing this into the work you’re doing. What’s funny is that we’re leveraging the three-step model and what you’re deploying back out in what we learned at that Sip Session. It’s a great partnership. It’s a give and take and we’re helping each other succeed, which is fascinating. When you say healthy businesses, too, as it relates to this. What does that look like? In my thinking, related to your Sip Session, I don’t know if that’s one of the same.

In the Sip Session, what we walked through was three different very specific areas of focus. I’ve done that differently now. I’ve organized my thoughts better. That was a lot of tools that I put out. Now, the point of Superstruct and what makes it different is that it’s not my opinion. It’s about you. You’re going to guide yourself through the process.

Most of the time, businesses know the roadblocks that they’re running up against. It’s someone to challenge them on why they’re not completing that hard task that they know that they need to do and what the roadblock is for them to do it. The three different areas I lean into, the first is around who you are and what you have as a product that’s unique in this world and what’s the message that you’re sharing. That’s step one. That’s your why. That’s why you get up in the morning, the resources that you have, and the practical matters of your business.

The second area of focus is on understanding that trifecta of opportunity that you’ve been building. Most of us forget about the fact that we need partners in this is to be successful. This is active, passive, and referral. That’s the way we think of that. That’s a three-point system to your success. If you imagine yourself in the middle of that, you have different tools, processes, approaches, and conversations that are going on all around you. It’s about embracing it and strategically seeking the right partners in each of those categories.

The last area that we focus on is that repeated consistency, which I would say is the hardest thing for me to do exercise. That’s the, “Here’s the roadmap. Here’s what we need to do to achieve the success that we want to have. This is what we have to do on a daily basis to harness that ability and hold ourselves accountable and be extremely rigid. Almost militant in our approach to getting where we need to go.” If we don’t do it, no one else is. This is the part that all of us fall short on. I have to do it for myself, too. I have to get up every day, even if it’s on a completely different schedule than I expected it to be. I still have to do the work.

What are some examples in that last category that you had to be rigid about?

For example, we have quarterly goal setting where this is where you want to go this quarter in both product, brand, and also your sales channels, active, passive, and referral. We break it down even further by two-week segments within a six-week cycle. Each of those, you have two different groups. You have one where you’re actively pursuing that growth and that’s on an upward side of a staircase, let’s call it. You plateau and you have to even yourself out.

It’s two six-week segments of an overall quarter. Your goal is to be able to get that opportunity done by breaking it down into tiny bite-sized pieces that are achievable for you. Once you get through that exercise, then you evaluate it with a very clear set of guidelines, and you micro-pivot. You make adjustments based on the things that have not worked and that enables you to meet your KPIs.

You make it sound so easy.

When you break it down, it is but getting yourself to break it down is so hard.

I know you have a lot of resources on your website. If folks could book some time with you to learn more about that. I’m curious, I imagine this is for folks that are finding ways to bring their passions into new businesses as founders. What are the businesses, sizes, and types are you looking for to partner with?

Sub 50 million is my sweet spot. We do work 0 to 100 million. If you’re interested in our resource network, that’s going to be around $2 million to $15 million or $2 million to $25 million in terms of fee prices that you’re going to get. That’s the sweet spot of the companies that we’re working with. There’s a lot of work that can be done on your own end.

Our product is very affordable. It’s four hours and it costs $5,000 or you can do it all for free. There are tons of materials on our website, We also have a webinar every week for free. It’s all on the event portion of our website and recommended books. We have interviews with all of our past history interviewees like Brent, for example. He had a generative listening conversation with me and that’s posted.

You can learn a lot of this stuff on your own if you want to take the time or I can run you through a four-hour session. I have a wonderful team that does this alongside of me each in a different subject area of expertise. Depending on who you are and the things that your business does. The only thing that you need to have is a desire to do it. A desire to see the challenges and go towards them as opposed to a way to be willing to listen and to be generative in your listening with me.

Depending on who you are and the things that your business does, the only thing that you need to have is a desire to do it differently, see the challenges, and move toward them. Share on X

The other component that’s important is that most companies work great when they’re at an inflection point, where they need to rally around the table together as a team and all flow into the same idea. As a solopreneur, it’s very easy for me to run through this exercise with you but it’s a lot harder because the feedback loop is only you.

I’m going to lead you to water but I’m not going to tell you what to do because the reality is that’s on you to figure out based on your unique business. I’m not going to learn your whole business in four hours. There’s no way. I’m going to help you learn how to deal with your company in a different way than you had before, and ideally build in a sustainable manner.

I’ve seen some of the output from the work you’ve done with Brent and pictures of all the activity. I could just imagine. You and four hours with someone going through all the questions and the challenges of thinking the models. I applaud you because it’s not only intent. It’s so amazing and powerful what happens. As you go through your model in your way of inquiry and working together to come up with what you can come up with, it truly is fascinating. I know it’s helping Brent as he moves forward in his career and his take on Be Generative, the company that he’s starting up and you’re helping him with. It’s fascinating to see what happens.

Me, too. He’s like the perfect case study because he not only listens. He iterates and does the things that are important to do. Not only in that session but immediately following the session. He was thinking through it and iterating on it in the most imperative time to do the work. He was making change. It all aligned in a beautiful way. I truly applaud him. I love that you two are working together on this because it’s going to be the most beautiful and brilliant product of all time.

It’s exciting. I appreciate that. It’s time when we step in and do more by the way we are versus all the doing we do every day. That’s one of the themes as we roll this out. Again, thank you for all your help on that. As we think about it, for the reader too, this is something I hope people lean into. Not only the listening side yet, taking you up on what you’re doing.

Running To Your Passion Projects And Goals

I’ve heard a lot of people have a lot of passion, side projects, and side hustles. What’s your take on getting those to become big companies or to be full-time jobs no longer side hustles? I imagine you’ve had these conversations with different people that, “I got this paying job, but this is something I’m trying to go towards,” as you would say.

There’s an opportunity to pull the right levers. You have to know what that right point is for yourself because you have bills to pay and families. There’s a lot of risk on the table to do it. Again, when you run toward the passion and the goals that you have. It’s undefeatable and it’s also undeniable in the sense that you have to do it.

For me, I can be part of that whiteboarding planning session with pleasure because it’s so much fun to watch somebody with big ideas come to the table. The way that we would approach it is by mapping out what that breaking point is for them, where they feel confident that they can break off and go into the next stage. There are a lot of tricks of the trade like stashing cash and building up different strategies around partners and boards, where they can leverage and get your product to market quicker.

You also have to want to do this. You have to want to be a founder. It’s a different lifestyle. It’s almost like a practice session with a two-week vacation, where you teach yourself what it’s like to be a founder and see if it feels right. Those are things that I would recommend because it is an acquired lifestyle. Most of the time when you’ve sat behind a desk and your only responsibility is to do the work that someone else tells you to do and you decide that now it’s time to do this.

There is a learning curve to the amount of things and the lack of resources available to you. At the end of the day, it’s on you at that point. There’s a lot of opportunity to think through that in advance. We have tools and friends that do those things and can provide the materials to you to support you through that process.

Women In Finance

You step in and do the work. I love how you’re a founder. You’re in different facets of opportunities and companies that you’re working with Star Strong Capital. How does it feel being a woman in finance? The way you connect the credit industry and helping people raise revenue instead of capital initially. For you, how do you compete? Tell us more about that. How does that feel like?

I’ll talk first about the finance side because it’s relevant. The reason Superstruct exists is because we originally thought we were going to do more of a spin-up studio model, a venture studio model where we would invest equity. What we realized, though, is that in the market, here’s the need set. We have unhealthy businesses. The businesses we see on the capital side, even if we had endless capital. We don’t have enough amazing deals all the time. We’d have to work hard for those deals.

Now, we get a ton of deal flow. There’s no question but a lot of those deals are on market. What we were looking for when we were at an $80 million fund only with fund one. Now we have fund two, which has changed the game a little bit. On the fund one side, we have to have a particular ratio for the deployment of capital to the position that we’re in. It’s a percentage game where we’re always playing with the levers around the percentages to make sure we don’t have too much capital in one position.

That does mean at an $80 million fund that we have a lot of little positions. When I say little, we’re writing $2 million to $10 million checks on fund two. There, we would be writing checks $500,000 to $2 million. They’re different businesses. The EBITDA structure is different. The quality of the businesses is different. What we find as their challenges are different. The most important thing is to never get overleverage.

On the healthy business side, we know now that there are a lot of things that we can do as a result of what we’ve seen in the market on the Superstruct side to help these businesses and that’s important. Start healthy. The other thing is that we used to write loans based on whether somebody was going to take us out with a lower cost of capital or an equity bridge and equity in the future. We were almost like a bridge to equity, even though we weren’t. We’re a term loan but a slightly different approach to it.

We can’t do that now because equity isn’t as interested as they were in the past. We can’t guarantee that we’re going to get the capital taken off of our books or we’re not going to get that position taken off our books. When we started to think formulaically about what the market needs, we need to help these businesses who are in our pipeline who can’t receive a loan now because they’re can’t service it successfully. We need to run them through a different approach.

In theory, that company gets to be healthy enough that they own their own power. They don’t need to be diluted further with equity. Years from now, they can come back to us and get a loan. That was one problem solved. One of the other things that’s an incredible learning that we did during our strategy review is that 75% of our book is female and 50% of our book is not White. That’s a important distinction for us.

There’s an overlap there but the fact that people find us is because the market needs us. We have a different approach to how we do things. Also, the companies in our purview, especially the female-founded companies, they think differently about capital and building a company. They’re much more strategic. They’re very thoughtful in their approach.

They have a ton of EBITDA on an annual basis, but then they’re also sitting on a bunch of cash. That model doesn’t work great in the venture capital community because their theory is you need to keep deploying capital into the market and that’s how money gets made. If you’re sitting on $2 million in your bank account and it’s not earning anything. That works against you. The feedback we consistently get on the capital side is that we are willing to listen and that’s our differentiator.

I do feel that we are interested and curious generally in businesses but our investment strategy has been to make sure there’s mutuality and that we’re willing to work collaboratively to get to the other side. Also, the things that you say that you’re going to do from a milestone perspective, you are going to do. We’re going to work alongside of you to make sure that you do those things. That’s important to the success of both your business growth, but also us paying the loan off. I have this very different opinion about women in finance and women founders, which I know I shared at the beginning that I wanted to get out. That’s there is a deficit on the amount of capital that’s deployed to women on the venture capital and private equity side.

The number is like 2.8%. Sixty-five percent of all businesses are female businesses. It’s a huge percentage of our economy. It’s like 45% of our economy. Those statistics are accurate. If you break it down, women are building businesses. We know that they are but they’re doing it differently. When a venture capitalist serves a term sheet to a woman founder or a female founder, there’s a different approach that person wants to take.

That woman wants to build her business differently. She wants to create something different than what a male counterpart might want to do. They also are much more transparent and real about how they’re going to get there. It’s a different approach and that definitely has something to do with why there’s only 2.8 % of capital in the market geared towards females.

I applaud you for what you’re doing and as you said, the market needs you, and so do the founders and all of us when you think about the diversity of the ideas and thinking and getting the money put back to work, the leveraging. Raising revenue to continue to apply it and put it to work.

In theory, that’s my goal for working hard every day. The theories keep evolving, but I would say that it is working.

You’re doing amazing work. You’re not giving yourself enough credit. I understand you want to keep generating, evolving, and keep it going. You have these aspirational goals that are huge. I saw something on LinkedIn. Even on your headline, it says, “Creating a thousand healthy businesses by unlocking roadblocks to growth and raising revenue.” That’s pretty cool. You said you believe there’s a better way. Let’s invest in it. Let’s go. Let’s invest in the future.

That’s right. There’s an opportunity here we’re sitting on. It’s time to go. It’s go time.

I love that you’re surrounding yourself with what you’re telling the world and what you’re doing. You’re following it through. Everything you’re talking about it. You’re not just telling the audience to go do this. You’re living it and practicing this. You’re getting better at it. You work at a pace that’s different because you know this and it’s working and you’ve seen it work well.

I’m a part of that as well. I see how it can happen. For the readers, slow down and take in this information. One thing I would suggest is to listen to some of the pauses that stop you in your tracks today or tomorrow. Start to allow or discover some of the things that Rache is talking about because right from the top of the show, you’ve mentioned how powerful that is.


One of the tools I have available on my website is called micro-pivots. It’s something that we learned probably in the third grade, all of us together collectively. It’s called Stop, Start, and Continue. Does everyone remember that? There are a few of them. There’s like red light, green light, and yellow light. This idea where you’re every day, at the end of the day, you take five minutes. You write down on a piece of paper, “What are the things I need to stop doing that are providing me with a negative feedback loop? What are the things that are not serving me? What are the things that I should keep going on that are working well?”

The other are, “What are the things I wanted to start working on that I haven’t quite yet done?” It’s putting yourself intentionally with five minutes on paper to outline those things. It can be around your kids, your community, and the things in your household. Whatever it is, that is something that I believe everyone can do to start looking critically at their lives and having the most intentional life that they want to live.

Start looking critically at your life to design the intentional life you truly desire. Share on X

We’re holding that space to allow for what we want. We’re stopping the things that are holding us back or clouding our day. We’re creating that space that allows us to discover or connect or align to our biggest purpose or our biggest desires or everything you’re talking about. You have these aspirational goals. You keep aligning to these aspirational goals and it’s these pivots, these stops and starts and continues. I love that because it’s like these are things we can all do.

If I have time for just a quick story. I have this interesting thing that I’ve always felt, which is I’m that person and Robert Frost, where you’re at a crossroads and you go down a path. I’m classically that person. 

Two roads merged and I had the other one. I endlessly have gone in that direction. I’ve just flowed through life. I have a wonderful high school friend whom I met through my high school network called Lane. She’s had the opposite. She’s been critically intentional about every choice she’s made in life from where she went to high school to where she went to college, where she lives currently, where she works, and who she’s marrying. The entire package.

I am not sure which is the better path. I have no idea. We’ve talked about aspects of that but it’s an interesting component to think through when you are a parent because I don’t know the right advice to give to my children. The advice I give to them is this micro-pivot, stop, start, and continue. The things that are not serving you, that are serving you, that you want to do, then that should in theory shift you.

Micropivot. Stop, start, and continue. Stop doing the things that aren't serving you, start doing those you want to do, and continue doing those that are serving you. Share on X

It does shift you because those are the things that I’ve done in my life to get where I wanted to go. I did not start in 8th grade saying, “This is the high school that I want to go to, and this is the life I want to have. This is what I’m going to do when I grow up.” As a result, I’ve had this robust and very interesting life.

I’ve lived in tons of countries. I’ve lived all over the country. I’ve had an opportunity to be married to two guys and have great kids. I have had lots of animals and wonderful life experiences. I feel like a robust person. The intentionality behind what I was doing and how I got here has not been there until now. That’s interesting, too, but I feel ready to make the choice on what I want to build with the last chapter, let’s say.

Building off your previous experiences. Not throwing it out, just getting better and what you were finding. As you think about it, we all have problems and struggles. We’ve all had changes. Even on your website, you talk about how you have a windy history. We all have that. I’m curious, Rache, are there some things in your life that have shaped you that you’ve had to overcome? I know you’ve had that big change from Guatemala to San Francisco to Connecticut, which is a big one. Are there other things that you reflect on that you said, “That made me learn it’s showing up now or it’s allowing you to think differently?”

It’s everything. I could start at the very beginning. I had a citric acid allergy as a baby. That’s a weird one.

I’ve never heard of that one.

Imagine every strawberry that you eat, you blow up. That’s a weird one for a kid. That shaped me. My dad had a terrible form of leukemia when I was 13 and 14. As a result, he had a stem cell transplant and is still surviving, which is wonderful. He’s had a lot of challenges as a result, but it also shaped my life from a health perspective.

He also married his nurse and who has been my stepmother in my life for nearly 30 years. I have a beautiful stepfamily of four stepbrothers and sisters. They’re all married with two kids apiece. My mom remarried also to another family. I have eight brothers in total. We’re eight. That’s a huge number to have in your life as siblings. That’s been a big shift.

Being a parent is probably the biggest one. I’m not sure I was supposed to be a parent or thought that I was supposed to be a parent until I had children. Now, it’s rooted in my soul. Everything that I do is for generational growth and change as a result of my children. I believe that if we do not give back to the future of these children, we don’t have one. That perspective has guided me in a big way and interestingly now as I start to rebuild my love relationships, that’s played a key role in the type of relationships I’m choosing next both in friendship and relationships.

If we do not give back to the future of these children, we don't have one. Share on X

I found that a lot of people want to go out in style in this life. They’re not interested in the next generation of change. It has flowed through every part of my soul from the car that I drive to the house I live in and to the clothes that I wear. Everything that I do is with full intentionality about the future and that’s a big shift.

Can you do a little fun exercise, so stop, start, and continue? Is there an example that you’ve gone through recently that aligns back to that? It seems to me that you’re true North.

It is. Thank you for that. Stopping, I would say, the big one is alcohol or any toxin of any kind. My son has a unique new food allergy set that we weren’t aware of. He was having these crazy meltdowns. I’ll give you two different versions of this, one for me and one for him. Both of us play into this scheme because I’m also a highly reactive person.

When he starts melting down, I melt down with him, which is not in the exact same sense but I start to panic on the inside. All of my nerve endings were crushing. I’m sure a lot of parents out there with kids who lived through COVID, you know what I’m talking about. You’ve been dealing with similar situations. On my side, the things that I needed to do to control it were to stop drinking because that aids in the expansion of stress.

I needed to start sleeping more because I can manage and deal with my life better when I sleep, and I exercise and drink more water. Things that I need to continue is listening. I need to listen to what he’s saying and not be the status quo of continuing to let him do it. What we did is we started him on a testing cycle. We went to a psychologist. We also did something through the school but then we learned to start digging into it.

We learned about heavy metals from COVID shots. He has leaky gut syndrome from meat, white potatoes, gluten, and weird things like yellow dye, which are causing him to have these crazy. His diet has been meat and potatoes. He’s a meat and potatoes kid and we’re vegans. It’s been a funny relationship, to begin with, but now we know. It’s all organic meat. It doesn’t matter. The kid has leaky gut syndrome.

On his side, we started giving him activities that were healthy like biking every day after school, playing games, and critical thinking. He’s a super smart kid. We’ve enrolled him in activities that he would enjoy. We’ve also started taking him to therapy and going through these three different channels of testing. We’ve done the blood work, diet work, and heavy metal work, and the spit test for DNA testing.

That was interesting. What we’ve continued to do with him is hug him, hold him, and love him every time he has a meltdown. What we’ve stopped doing is the reactionary stuff. We’ve tried to say what’s going on with him, but he can’t control it. It’s not about yelling at him and telling him no. We need to do things differently because that’s not going to affect him in a positive way.

Those are good examples. Thanks for sharing that. It’s so incredible the impacts that we can have based on our responses and how we handle our day-to-day interactions with family or people we work with. We almost assume certain things happen for the wrong reasons. These are things that are out of his control. I appreciate you sharing that. We can apply that in so many ways.

Leaning Into Your Uniqueness

It’s like when you go back to the business and we talked about this before. We can keep trying to do the same things that everyone else tells us to do. The reality is, our business is unique. We are at our own snowflakes, too. We have our own DNA and our own human design as a company. We need to lean into that uniqueness. Otherwise, we’re not differentiated from the market.

The other approach is that other people would do it if it were easy. We know that. We have to guide ourselves through these unique core values that are different from us. The only way to do it is to lean into the things that are working or not working and figure out the next plan forward and micro-pivoting. I don’t ever recommend someone pivots. You need to do it on a micro level, test it, ensure it, and know that it works, then move to the next one.

I like that. I have the same with how we change habits. Habits are going to be until we find better habits or better pivots that you’re talking about. We have to learn and get some good feedback. We get some good results. We’ll do it again. I want to do it again, which is important. Rache, changing gears a little bit. I’m curious about what brings you joy. What’s your take on happiness?

Live Your Possible | Rache Brand | Generative Listening

It’s such a hard one for me. It’s such a loaded question. You can’t be happy. You know this, without being critically and critically sad. You cannot. It’s like you don’t know the different levels. I have had the hardest and most traumatic experiences in my life than I could imagine that are so devastating. When I find things that are joy-filled like hanging with my friends or hiking with my Husky, Kira, or doing something hard and accomplishing it, and get that euphoric dopamine. All of that to me is just next level. It feels unbelievable.

For me, I like healthy exercise. I love dancing with my friends. I love hosting crazy parties. I should be like a full-time host of a party that’s my own party. I have a great group home. I live in New York with a bunch of friends that I’ve known for a while and we all are roommates. It’s been pretty epic. We host pretty crazy parties. Our goal is that we have never met the person that we need to meet in order to realize all the potential that we have. That is what we lean into every day. As a community, we build and we are creating the future.

Creating Our Future

You’re creating the future, so it’s possible we can create our future.

We are creating new drugs and new systems. Drugs like health drugs. We’re creating new food concepts, new technology, and software solutions. We’re creating that ability to believe in what’s next and do it differently than the way it’s been done.

I’m with you. I’m just having a little fun. I do believe we can shape our future. It’s everything you’ve been talking about, which has been amazing. It’s about holding that space for us to discover, create, and connect to our true North. What we want to create, if it’s more joy or a new invention or being all-in new business or being there for our family. Whatever it is that we bring, we got to hold that space and do exactly what you’ve been saying, listening and stopping, starting, continuing. I love that. It’s so simple. It’s applicable.

It’s so cheesy but I love it. It’s such a funny thing for me to use that because I’m pretty sure my dad was drilling it home in my head when I was in third grade.

That’s so good. I also agree, to go back to the happiness point. I’ve been one of those people that I view happiness as it’s all within. It’s all there for all of us. I didn’t recognize the depth of it and to your point, until I shared the other emotions. I’m going to go forward. Let’s make it positive and happy but when I recognize the bold ability, the riskiness, the sadness, and the frustrations. When I recognize that, that’s when the other side of it does come out brighter.

When we have times of darkness or down times, we can pull through that a little bit faster. A little bit smoother knowing we’ve done it before and we can. We’re going to survive. We got to take these micro-pivots, even in those times to work our way through it. I appreciate your take on happiness and how you’re bringing that forward.

I’m all ears to learn more from you. Thank you. Teach me.

Before we wrap up, is there anything else you’d want to share with our audience? Certainly, we focus on helping people overcome challenges, to lean into their passions, believe and trust what is possible, to wonder, and to go on that side of what we can become. I’m curious if you have any final thoughts around all that.

It’s because you have blue eyes and you match your shirt, I keep going from your shirt to your eyes, and this contrast of live your possible in pink. The whole time I’ve been looking over at Live Your Possible. This amazing thing for me happened, and I have to share it because it’s so true and evident with what you’re building with the stories that you’re sharing and also just what you and Brent are about to do.

You are your own glass ceiling. We are all our own glass ceilings. It’s like betting on yourself. Live your possible. Live the opportunities that you can control, the things that you can dig into. You’re so unique. Each of us is unique. We forget sometimes that the roadmap that we’ve been on like falling in suit with the things that our parents wanted for us or our friends expected of us.

Dig one layer deeper and go into who you are and what you need to do in order to solve some of the challenges that you’re running up against you in this life. Nothing is left on the table or shouldn’t be left on the table. It’s up to us to decide what we do. Bet on yourself, break through your own glass ceiling, and live your possible.

Live Your Possible | Rache Brand | Generative Listening

Rache, thanks for being here. here. I appreciate everything you’re doing. It’s jumpstarting our community in Connecticut. I know this is going to impact globally as well. I appreciate you. I love our friendship and I look forward to getting together and to go through some of the sessions you talked about because I could benefit. I’m looking forward to how we can help each other live our possible.

I love that. Thanks so much. A pleasure to chat.

Important Links

About Rache Brand

Live Your Possible | Rache Brand | Generative ListeningRache Brand has been a founder, an operator, and a builder. Her journey is windy, but aren’t they all?

In 2022 she transitioned into private credit and this has been the most rewarding part of her journey to date.

She joined Spring Hollis in her private credit fund Star Strong Capital, and together, they built an advisory practice specifically to help businesses sub $50m stay in the market and grow.

Star Strong Capital: Chief Operating Officer for their private credit fund, which is a delayed draw, term loan with $80m AUM. They are currently raising Fund II.

Superstruct: The advisory service business, provides an affordable workshop with a 360º Assessment + Growth Plan. It offers 3-next steps to help the business raise revenue while remaining net positive.

Rache and Spring believe in a positive sum mindset, working in the same direction towards growth.ii

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