The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

1,335exchanges match
892on raw tape
51redirected or not addressed
Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q How often do you think people fail at listening?

A Very, very often. We record all of our mentoring sessions and many of those are pitch practices and we send people the transcript and we send them the recording and say, here are the 20 things you should fix in your pitch or your business plan or whatever. And when 18 of them are, are broken in the same way in the next area, they're, they're not listening very well. They're probably not going to make it. If they say, oh, the customers don't really know what they want. They don't, they, they actually talk to customers, but don't listen to the answers, or they go and rely on SurveyMonkey multiple choice questions and try to count things up before they know the right questions. Um, these are, are all very common ways to, to not, to not listen. You figure that probably, Nine out of 10, maybe 19 out of 20 of the companies are failing because they're not listening. Most of those three quarters of those are because they're not listening to their customers.

AI assessment note: “Very, very often. We record all of our mentoring sessions”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q because of all the problems, there's constantly problems, right? It it's never like everything is working smoothly. There's something is always breaking. Um, so I didn't want to do that. So you get into software development, you've been in software development for 20 ish years. How have you seen it change? And I guess that's more towards now where AI is coming out and being more relevant in the process.

A The pace of change right now is insane. I'll just say that. It took, it was a little bit of a, we saw a lot of progression in those early, you know, nineties to late nineties when tools started coming out into the marketplace to make it easier for designers to code. You know, what you see is what you get editors. The Dreamweaver tools. Microsoft front page was an early iteration of what you see is what you get out of there. And, uh, those tools were meant to expedite the development process by removing the need to manually code a lot of stuff. If you think about it, it's, it's a lot of, um, uh, editors that gave you the ability to affect or implement CSS and styles and templates and, And stuff to, to make it faster to produce what you wanted the user experience to be. The same thing was happening on the back end, but that's not the world that I came from. I was more on the front end design and engineering side of things. So today, I think what we're seeing is just the pace of which AI tools are now coming out to basically do the same things to expedite the development process. But now instead of utilities You know, in a control panel or dashboard there, you you're using to put things together where it's doing the coding behind the scenes based on what you're clicking and what you're selecting. Now you've got natural language prompts that you're using through these AI tools to g…

AI assessment note: “today, I think what we're seeing is just the pace of which AI tools”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q With Thesis, you're trying to help companies figure out their own UX journey, right? And you're trying to use like text-based or voice-based or visit visual agents to make them do that.

A We are a generative UI company. What that means is that, again, this is not something we came up with. It has been talked about and written about a lot, but what we are saying is that CLLMs are great. But text is probably not the best representation of your data all the times. For example, let's take a practical example. You want analytics use cases, right? You want to drill into the history of the US population growth, understand the peaks and troughs, slice and dice it by gender, race, immigration, stuff like that, right? Now, even today, you can go into chatgpt.com and enter all this, like, tell me the population of US, how did it grow over last 10 years? And it would keep on responding with text.

AI assessment note: “We are a generative UI company. What that means is that”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Frustration. What, you know, like you, you've got a goal in mind. You're willing to be frustrated in order to work, right? The only way out is through. So imagine if you stopped at the first sign of frustration, that means that whatever you're pursuing, you don't want bad enough.

A True. Yeah. I, I want more than anything to be able to have enough money coming in each month. Cause it's, it's, it's different to have assets, liquidity, net worth, and to have income. And many years ago I built net worth, but I never figured out how to build passive income. And so I have to keep working in order to make sure that I don't burn the money that I've already saved. Cause I was very fortunate at a very young age to make a lot of money. And that's been my frustration is making sure I don't burn through what I have while also now being able to create active income so that then I can have enough coming in that I can afford to give my parents so that, that it doesn't affect me. So, so I can live on it. They can live on it. And my dad can retire because he's tired and he doesn't want to work anymore because he's a dentist. Imagine 45 years of your back like this. And your hands like this in people's mouths and he's just in so much pain. So I want him to be able to retire, but he can't afford to retire.

AI assessment note: “And that's been my frustration is making sure I don't burn through what I have”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Okay. And of all of those businesses, which was the one that was most exciting for you?

A The e-commerce business was the most exciting at the, um, probably because there was a new industry being opened up. In addition, the scale of that organization was national and international. So we, we were working with very large Distributors at the time, uh, I think one of the largest or the largest HVAC distributorship in the world. We were working directly with manufacturers. We were, um, working with 30,000 contractors across the US. I built the computer systems to manage that and, um, and generated a lot of strategy to create a A type of business that, you know, didn't exist at that scale before, um, because we were opening a new, we were opening up new channels, new distribution channels in a very closed industry. So that was, that was pretty exciting. It is different than that sort of, that sort of work is different than, um, you know, creating a better mousetrap. You know, when there are already mousetraps that exist.

AI assessment note: “The e-commerce business was the most exciting at the, um, probably because”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Yeah. So how did you use this energy to get into a business that would become stable? And what, what, what, what was your idea of like a business that you could run that would allow you to use your energy in a positive way?

A Yeah. So my first business was actually writing business plans for startups, which I learned on an internship that I took over in Australia in college. That didn't do too well, but it ultimately transitioned into what I, I, my first really successful company. But when I got out of JP Morgan, I realized you have to have some type of intent. You got to learn how to get attention in order to monetize things. So I read a book called crush it by Gary Vee, which talked about personal branding and how it's your resume and it's not going away and it's a major trend that's going to continue. So I started a personal brand. But I had credit issues from all the, you know, years of destruction and all the debt that I had. So I learned how to get late payments collections off. I learned how to remove my utilization. So the debt that I had over to a business credit when I started some companies so that I could have my utilization lower and increase my credit score. So I got it from a five, 24 to a seven, 93. And at that time I was running a marketing company. With another entrepreneur running ads for chiropractors, doctors, dentists. And while I was doing that, I was personal branding really heavily and teaching about credit and the process that I took my credit from a five, 24 to a seven, 93 did that all on, on Instagram shared tons of things about credit and travel hacking. People were aski…

AI assessment note: “So my first business was actually writing business plans for startups”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Are there any tools that you use in the business that are lifesavers for you?

A There's quite a few, uh, because of the performance marketing side of things, we'll use, um, one, like one of them, for instance, is called Bright Edge. Uh, they're a enterprise level SEO company. So it allows us to get an idea of what organic terms people are using to find things. Well, organic happens to be one of the highest performing channels. So we want to make sure we're aligning ourselves with a premier You know, uh, SaaS company that we can borrow off of, which again, right now in the movement of AI, they're able to predict what's happening, or they're able to, you know, put new signals out there for how the search engine results page are showing up with conversational results. So that's one as an example. Then we have another one that's like what's called Resonate, and that's what allows us to understand audience behavior and motivation. And so now we can target down from 34 to 37 year old females That live in this particular geography and these are their habits and their spending behavior. And so that gives us like an understanding of who they are that we could then target, you know, and not to say we're going to target them specifically, but from, from an aggregated data standpoint, we can target, you know, people that, that fit that persona. So that's another one. And then of course, Google analytics, which really shows us all the different, you know, behaviors on …

AI assessment note: “one of them, for instance, is called Bright Edge. Uh, they're a enterprise level SEO company.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q How did you get your first student? Did you, like, were you creating the content as you were looking for students or did you create the content and then test it on someone you knew? Did you do free trials? Like what did you do?

A It's kind of a funny story because I, um, for several months we just concentrated on building the curriculum, right? I mean, we literally went through every question in the quizzes from the curriculum that we were using and then looked up What, what page number and what paragraph the answer was on because I wanted to be able to navigate it. And so after these months, we're getting close to finishing our online system. We'd chosen a learning management system and LMS and we were programming and everything. And I said, okay, turn on the Google ads. I want to see, you know, how long is this going to take? You know, I didn't know really. I mean, I had some idea on Google ads, but I didn't understand, you know, would it take a little time to ramp up? So we, We turned it on and the phone rang like an hour later and someone was saying, yeah, I'm interested in your training program. And I, and I was so surprised. I remember just kind of going, ah, yeah, yeah. Okay. Um, you know, Um, and I remember calling my web designer and say, shut it off, shut it off. We're not ready yet. But it was exciting to know that once we turned it on, all of a sudden the phone started ringing, right? So we use Google ads for, for, uh, several years until we built out enough content and, and mastered our SEO to, you know, pretty much own the first page of Google like we do now. So organically. Which is nice.

AI assessment note: “We turned it on and the phone rang like an hour later”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Okay. You said the term non-destructive testing. I was going to say it in the intro, but you might as well tell us what it is. What is it?

A Yeah, I guess. Yeah. You know, it's funny because people say, you know, uh, electrician, plumber, HVAC, roofer, everybody knows everyone's nodding when you say that. Yeah. Oh yeah. Yeah. And then you say non-destructive testing in their head. Tilts, and they look at you a little funny. So, you know, non-destructive testing is utilizing radiography, so taking x-rays, um, is the layman's term. You know, we do radiographic inspections, industrial, ultrasound, magnetic particle, liquid penetrant, visual, eddy current acoustic emissions, all these different modalities to test structures during the manufacturing phase. Define flaws, discontinuities, something that might, uh, be a problem and create the product to fail. So, um, non-destructive testing really touches on so much that we really don't know, like all the lug nuts on your cars while they're being manufactured are batch tested. To make sure the quality is good, right? Um, structures, spacecraft, aircraft, bridges, nuclear facilities, pipelines. We do training for Lockheed Martin, Boeing, SpaceX, Blue Origin, um, you know, uh, manufacturing companies across the country, across the world. And, uh, so it's really a quality control. It's during the manufacturing and then after it's in use, right? Every time people have probably been on a bridge before walking and they feel cars and it rumbles, right?

AI assessment note: “non-destructive testing is utilizing radiography... all these different modalities to test structures”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q uh, to be fair, it was a good bit more than what you just mentioned. Um, so What was the most expensive thing that you spent money on or that you, yeah, I guess what's the most expensive thing you spent on? And it doesn't have to be a bad thing. It could be a good thing. Something that like you love that just makes you feel good about yourself.

A Yeah. So I, I would say the, the biggest advances, cause I don't, I don't kind of look at things like now when I spend money, I, I spend it on purpose. Like I'm a purpose spender. And so like, for me, um, the biggest investment I would say That I've made was on a coach. Um, the greatest investment was on a coach, and it was probably about 55,000 dollars, but this coach actually had the knowledge that I needed to break into. Um, and literally, um, by learning the concepts that he had to teach me, I actually made, um, uh, had a multiple six figure day, right? So most, most business owners don't even have like six figures or multiple six figures in a year, but I was able to do that in a day just by leveraging This person's knowledge. And so that was like one of the greatest investments that I ever made in myself. But even before I got there, I want to say this, um, when I was a struggling entrepreneur, I didn't really understand like the, the purpose of investing in myself. Like I was a very cheap person. And so when I would go to business and networking events, and then they would have these vendors, um, of all of these different, like, um, MailChimp would be there and like, Square and like all these different people that are like, use this service. It'll help you grow your business. You know, pay me 25 dollars a month or pay me 50 dollars. I'm like, nope, I'm gonna do this by my…

AI assessment note: “the biggest investment I would say That I've made was on a coach”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q All right. Thank you for that. Uh, what made you want to do this? Especially if in the past you had other businesses that it sounds like were more profitable.

A Yeah. Great question. So one was just the natural evolution of things. And two, um, my seven plus figure business had employees. It was manufacturing. It was brick and mortar. And primarily we were, um, B to B and selling wholesale. So very different, um, processes. And stress levels. So I think you'll remember that that's when I experienced burnout because it was just this push grind hustle. And I really wanted to change. And I also felt to be an integrity to who I wanted to serve. I actually had to embody what I was helping them to do. And so that's like, I am so much more balanced and grounded in this particular, um, income bracket. Not to say that I don't believe that the sky's the limit, but I, I do believe that there is a level of scaling and team that comes when you get to seven figures that I'm very happy to have independent contractors and a VA every now and then at the six figure level.

AI assessment note: “I experienced burnout because it was just this push grind hustle. And I really wanted to change.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q So what was it that this business coach, business coach taught you that was so valuable that you were able to make changes so quickly?

A He basically told me, don't waste your time with clients, uh, meeting with clients if they can't afford your services to begin with, because you're just spinning your wheels. Uh, I went to about. By the time I met him, I went to about 53 client locations, and none of them hired me to give quotes. At the end of the day, they said it was too expensive. So not only did I waste gas in time going to all those 53 locations, no one hired me. So when I met with this business coach, he's like, just give them the price over the phone. Who cares? If they say they can't afford it, at least you just saved all the time and you can use that time somewhere else because your time is very important, not so much the money. And we started doing that. And we've been, we were able to reach out to more clients and we started closing more clients doing that.

AI assessment note: “He basically told me, don't waste your time with clients”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Yeah. My company ended up making a pivot as well. We pivoted, uh, to team collaboration for our software. So, but it, it's software moves a bit slower than everything else in that regard. Um, so then how do you discover bottlenecks in your business and how do you handle them?

A Uh, so the good thing is I worked in private security for a couple of years before I opened my own company. So a lot of the bottlenecks I found out was around paperwork and hiring. And client acquisition. So I spent many, many months, I believe it was about 14 months to perfect that procedure, just trying to see what worked or not. Because when I first started to hire my first employee, I was in the office with the guy for an hour and a half because he couldn't figure out how to fill out the paperwork. And it was annoying and he wanted to fill it out there to make sure he did it correctly. Cause we have a lot of forms, uh, that they gotta fill out. So I automated that process to where now it only takes him two minutes and it goes through.

AI assessment note: “So I automated that process to where now it only takes him two minutes”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q So what kind of things did you do on social media specifically? I'm curious from a security company point of view.

A So right now we're doing what we call the guard chronicles. Uh, and it's kind of like, Anonymously taking video from guards have been screwed over in the industry and we're posting their stories on how they got screwed over and what happened to them by other companies. We also have informational blogs on how security companies are illegally working with the client. Uh, for example, in the guard and the bar industry, you're not allowed to provide bar security unless you have a insurance and it costs roughly 23,000 dollars a year per client. A lot of guard companies don't have that. So they're leaving their guards, uh, their clients exposed to the point where now companies like us can no longer get insurance to do bar work because of all the lawsuits that happen with those companies.

AI assessment note: “we're doing what we call the guard chronicles. Uh, and it's kind of like,”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q So what was it that this business coach, business coach taught you that was so valuable that you were able to make changes so quickly?

A He basically told me, don't waste your time with clients, uh, meeting with clients if they can't afford your services to begin with, because you're just spinning your wheels. Uh, I went to about. By the time I met him, I went to about 53 client locations, and none of them hired me to give quotes. At the end of the day, they said it was too expensive. So not only did I waste gas in time going to all those 53 locations, no one hired me. So when I met with this business coach, he's like, just give them the price over the phone. Who cares? If they say they can't afford it, at least you just saved all the time and you can use that time somewhere else because your time is very important, not so much the money. And we started doing that. And we've been, we were able to reach out to more clients and we started closing more clients doing that.

AI assessment note: “He basically told me, don't waste your time with clients”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Awesome. I love it. I love your mindset, dude. I'm, I'm really impressed. How do you anticipate problems? Not only personnel wise, but like the market in general and how it affects your business.

A We look at other countries and other States, uh, to determine issues like when the COVID first hit in China and they were closing down. I told my staff, it's going to be a matter of time before it hits the U S and our state. Uh, so we, uh, we started reaching out to clients and we started telling them, Hey, you guys need to buy from us. Uh, I need to sign contracts before COVID hits because the prices are going to go up, locking your price now. We ordered uniforms, equipment, guns, ammunition, all ahead of time. So when COVID actually closed down our state, we had received the last uniform order the day before. So doing those kind of things, we anticipated right now, we're getting ready for the recession. I know it started. People are not fully aware of it, but it's going to hit hard in the next couple of months. And we're already starting to make preparations for that. We're buying equipment and we're buying other things right now while we can still get it and companies are still open, uh, just to prepare for that.

AI assessment note: “We look at other countries and other States, uh, to determine issues”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Okay, good. So, uh, can you tell me about this story? I was originally going to say, what's your most expensive mistake, but basically you've already kind of pinpointed it. Um, why don't you go into the detail of what that is?

A Yeah, definitely. Yeah, definitely. So biggest mistake, 850,000 dollar mistake. Now, uh, a lot of this did happen to iron itself out over the next year. Um, and I do have other mistakes we can always talk about later, but In the massive growth of business during the pandemic, during the beginning of lockdown, basically everyone wanted to buy supplements because they were wanting to be healthier or afraid or whatever it was. Our sales went through the roof, you know, from having a good month of a million dollars to suddenly averaging 1.5 to two million. Um, we had a particular issue, kind of two issues. The first was we didn't have enough protection on our credit card processor to keep scammers out. So if you use Stripe, which you can't really use in the supplement space, especially at scale or PayPal, they will close your accounts. If you are right now, look for alternatives, please. Um, but our credit card processor had one of like four different, um, protective tools on there. And it was the weakest, least expensive on my half version. And as we scaled, I didn't remember that. Didn't remember to tell them to turn the other ones on and pay the extra few grand a month to cover it. And we had about 300,000 dollars of Basically stolen credit cards with fake purchases on our products. And people were stealing the products, shipping them to this couple of warehouses in New York, an…

AI assessment note: “So biggest mistake, 850,000 dollar mistake.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Okay. And typically any sort of dividend that happens like again in a public market is quarterly. Um, some are single, you know, once a year. How do you guys handle payouts?

A Yeah. So ours are quarterly. So we do quarterly cash distributions. Uh, we have what's on our platform. It's called a, we call it our web street wallet, but it really just goes into your web street account and each quarter you can either withdraw those funds, you can reinvest them. You can let them sit there and grow. Um, and then reinvest, you know, whenever you're ready. Um, so yeah, quarterly cash distributions. And I guess one thing that's important to hit on is it's a two third, one third split. So because you're not actively running these businesses, right? You don't own, you have no say in what's done in the businesses. You, the investors receive two thirds of the profit every quarter. And when these businesses are sold, which is generally in the two to four year range, after you invest, you receive two thirds of the profit on the exit. So if it's a For let's say it's a million dollar fund has three businesses. They all grow to collectively to a million and a half that half million dollar growth is the investors receive two thirds of that when the business is sold as well. So two thirds, one through third split throughout the life of the business until it's exited.

AI assessment note: “Yeah. So ours are quarterly. So we do quarterly cash distributions.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q So if someone were interested, is it something like Kickstarter where you can see individual companies that are available to be invested in? Or do you say, oh, I want the e-commerce fund or I want the SAS funds. Like how does that work?

A Yeah. Right now the model is not seeing the actual businesses. It's seeing the type of type of fund and the operator that's behind that. So, um, because we've had such a long history in the E-commerce online business space. We have a big network of people that have bought and sold many sites, right? Over the years, they've come to the marketplace, empire flippers or otherwise, and bought and sold multiple sites. They have a good track record. We bring them on because they, well, they have different reasons for wanting to come on board with us. Some of them want to do buy bigger and larger businesses than they've been able to afford in the past. And, um, uh, some of them, you know, just want to implement their strategy again on many, many different businesses, but whatever the case is, You come say, see like, okay, I want to invest in this fund because it's in the SAS monetization and I trust this operator's background. He's built and sold five different websites or five different, uh, softwares. You know, he's got a great team behind him and you get all of that information ahead of time. You can see what their track record is. And the last thing I'll say on that is, uh, a lot of these operators, they come work with us multiple times. So they'll come run a fund. They have a track record. They distributed, you know, 20% IRR over the last four years, and they're ready to do anothe…

AI assessment note: “Right now the model is not seeing the actual businesses. It's seeing the type”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q I've seen recently that millennials and particularly Gen Z believe that they need to make at least half a million dollars a year to survive in America. How do you feel about that statement in particular? And how easily can someone create passive income of half a million dollars a year?

A Well, I think it's really difficult to create half a million dollars in passive income. I mean, it's unbelievably difficult. And that's why almost nobody can do it. So, um, do I think that Gen Z needs to make half a million to survive? No, because you can look anywhere in this country and see that people don't. What I do think that is happening with these younger generations is that they are completely unrealistic in what it takes to achieve anything. And so, um, I, I like the concept of, Hey, if you don't have what you want, where you are, then pick your shit up and move, right? Like, Go somewhere that's less expensive. So I live in Montana. Um, we live outside a town called Bozeman. Bozeman's one of the most desirable places in this country for people to pick up from their city life and come move to the mountains. And people think that, oh my gosh, I'm going to come to Montana. It's going to be easy to live here. Well, we just had two weeks ago, -30 degrees, right? Everything froze. Um, people find out that, oh, well, guess what? Your septic system could have problems if it's -30 and all these things. Um, but more importantly is that what they don't realize is that the cost of living here is unbelievably high. So the median home price in town is almost 800,000 dollars. Well, with eight percent interest rates, you are not purchasing that home and having less than a six or 7000…

AI assessment note: “do I think that Gen Z needs to make half a million to survive? No”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q and so I really hope that you enjoy it. You have a 140 employees. You've been doing this business for a number of years, and you say you're always going through the process of change and trying to figure out how you can become more effective as a CEO. At what point in your business did you realize that there was a problem, that you, that you were the problem?

A I think that When I started to drink five cups of coffee by noon, and I remember my, my wife, uh, walking, this was, uh, this was maybe six years ago. We were at about 40 people, and, and my wife was asking me, uh, about, uh, why is it that I seem to show symptoms of acid reflux? And what could be causing it? And, and I was sort of trying to unpack this for her because we're trying to figure out together, like, why is it that I wake up with a raspy voice every morning? Uh, where is all this sort of, uh, where's all the stress coming from? And the five cups of coffee, the black coffee, no sugar by noon, I think was one contributing factor And then I re and I wanted to connect the five cups of coffee, like that, that act of drinking so much coffee to how did it make me behave? And it became pretty clear to me that I could not continue drinking five cups of coffee for the rest of my life. That wasn't sustainable. And that became almost like a symbol of I'm probably showing up as very manic at work. I probably am super obsessed about what we do. I'm probably driving some of my team members crazy. Um, and at the same time, I really care about my team. I really care about the customer. I really want us to do amazing work. So how do I stop drinking five cups of coffee? How do I Continue to deliver amazing level of service and create value in the lives of the team and the customer, but…

AI assessment note: “this was maybe six years ago. We were at about 40 people”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q What kind of consulting were you doing specifically?

A Um, so at that consulting firm, I was implementing, um, business applications. So CRMs and, and whatnot, and that's before the world of SaaS where, you know, you didn't even have the internet connection for, for, for those kinds of SaaS for, for, for internet bound SaaS. So, so I would implement Microsoft Dynamics CRM. I would go into companies and consult and run workshops, get requirements. Great experience to be able to translate technology, sorry, business requirements to technical requirements and technical issues to business speak, because nobody wants to know, you know, when you go, when you go to the garage, you don't really care if that specific piece in the car is broken. Will the, will the car function and Is it dangerous? That's all I want to know, right? Can I avoid fixing this for the next, like, three months? That's, that's what I want to know. I don't want to know the caliper of the disk, the fusion reactor of that. I don't care. I don't want to know this stuff, right? So, so I learned that early on in my career. I was 23 at the time. I learned early, early on in my career. And then I went off on my own and opened my own, uh, custom dev shop. Um, yeah.

AI assessment note: “I was implementing, um, business applications. So CRMs... I would implement Microsoft Dynamics CRM.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q What were some of the difficulties besides that in trying to take care for her?

A Sure. So my mother, uh, my mother and father divorced when I was a teenager. And even though my dad remarried, my mother never did. She lived independently, uh, sort of prided herself on her independence. Uh, But her ability to maintain the home, she lived in a fairly large home, a large amount of property, but her ability to maintain that slowly deteriorated. Her ability just to keep a clean, safe environment around her deteriorated. So I made the first tough decision I made for her after her diagnosis was moving in a professional caregiver. And she hated that. She hated this invasion of her privacy. And it wasn't very long after that that I realized that she was no longer capable of driving safely. Every time I saw the car, there was more body damage on it. And of course, when I spoke to her, it was never her fault. So taking away her car keys not only took away another source of independence for her, she had to ask permission to go anywhere. Really, really upsetting for her. Um, she had, uh, uh, mangled her finances and, uh, work with all of her creditors to figure out how we were going to dig her out from the hole that she had dug. Uh, she had developed hoarding tendencies, so we had a massive, uh, clean out of her home and, and, and, and property, uh, which she fought tooth and nail, uh, every day. Um, so it, and, and what made this especially tough, um, was my mom, uh, Wa…

AI assessment note: “moving in a professional caregiver. And she hated that.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And so when, how long was it from when you started to talk to doctors until you got the diagnosis?

A So at six months, we started talking with this pediatrician, um, Said, hey, you know, we think something might be off. She's like, yeah, we think something might be off too. It's a little early to get the diagnosis. So, um, he didn't start walking until he was two and he's, and he still didn't talk. And I don't think it's untypical for somebody to not start talking until they're after two years old. So we got the diagnosis at two, two and a half years old, somewhere around there. Um, when, when we thought that we could get A real diagnosis other than just some weird anomalies of, oh, they're not old enough to be able to do these things anyway.

AI assessment note: “So at six months, we started talking... we got the diagnosis at two, two and a half”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q How, what kind of food does he make?

A Um, so we, we actually, we go to the grocery store every day. Um, so primarily like hot dogs, chicken nuggets, you know, the, the, the staples. Um, and every night we go to the grocery store and he gets his can, most nights he gets a can of SpaghettiOs. Um, at the grocery store and a, and a treat. So, like a, a can of SpaghettiOs, um, like a little, like a little Debbie cake or a Hostess cake or something like that, and a drink, and It's, it works really well because we get to socialize him, go to the grocery store, he gets to walk around, pick his own food for that night, and then we go through the checkout, and then he gets to practice all those things. So that's how we've, um, that's how it just naturally happened for him to do his grocery shopping. He likes it. It's a nice activity at the end of the day, um, and then we don't have, Cause if we had 12 cans of SpaghettiOs, he would eat all 12 cans of SpaghettiOs that day. So, um, it tends to work out pretty well for all parties.

AI assessment note: “primarily like hot dogs, chicken nuggets, you know, the, the, the staples.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q start, not even being 40 yet. So I'm glad that you had a role model, someone to look up to, like your father. Did you ever get a chance to work with him, or to go to work with him, or see actually what he did, or did you just have this idea of like, he's important, or he seems important, and that was like enough for you, that image?

A No, there was a decade starting as, uh, delivering papers. My dad was in the newspaper business, so 10, when I was 10, I was a carrier girl, not a carrier boy. Um, and then I loved on Saturdays going into my dad's office, you know, if he had to do, if I had to do some filing or whatever it was, I was going in with my dad. Um, Part-time jobs throughout, uh, right into university. My dad would always find work for me and I worked for him probably just part-time in different capacities. Um, everything from doing the fortiori race tracks to running circulation ads to, so for about a decade, uh, I worked with, with my dad, for my dad, um, in that period, that very formative, formative years for myself.

AI assessment note: “for about a decade, uh, I worked with, with my dad, for my dad”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q got to see all of that And go, wow, running a business looks like it sucks. I don't really want to be a part of that in I've ended up in it anyways, but at least when I was younger, I got a sense of, of the pluses and the minuses of it all. So. At what point did you realize that you wanted to focus on helping women specifically?

A Well, for me throughout my career, and I started relatively young, my first tax season, I was 19 years old and it was all men in the accounting profession. My bosses, my managers, I had no female role models. And pretty much that was throughout till probably my late thirties, even to early forties. Where, where I worked, and who my colleagues were, and who my bosses were, were all men. And so, as a professional, I never thought, I, I'm a woman, I have to be treated differently. I just have to make sure I show up, and do good work, and work hard. So really it probably started for me in my about mid forties when I was showing up and there wasn't enough women in technology. So I was on the board of the Canadian Association of Technology Alliance, and I joined this board, 35 member board, and there was only three women. And I, and the chair of the board and the CEO said, okay, you, you are going to work with This organization called Springboard, but we want you to advance more women in technology. And this was 2003, 2004. I'm like, sure. I'm in. And through that, just that re realizing that women need more empowerment. Women need more role models. Women need support. Um, so I was able to create what we call the women in technology forum through CATA. And then from there. I was also advancing my career in governance. I was serving on boards by then, and I, there was not enough women…

AI assessment note: “So really it probably started for me in my about mid forties”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And so what was the end result? Did you sell that company? Did you get out of bankruptcy? Did you just fold? What happened with it? Because you said you moved into consulting. So it seems like you moved away from that business. Yeah.

A So what happened actually is that, um, we were an asset based lending, you know, funded business, had a partnership with a very large bank. I'll leave them nameless. And they Got nervous as we came in at 2008, 2009 with sort of the condition of our finances complicated story, but long story short is that they called our note. Um, at that time we had an eleven million dollar revolving line of credit. We had about 6.5 million outstanding. And when they called it, we couldn't meet it because of the timing of the year. And we went into this whole thing basically, which is forbearance. Um, during that forbearance period, I went out and found a private equity group who ultimately bought the debt from Wells Fargo and then leveraged the full value of that debt through the bankruptcy process. So I actually took the, Business through the bankruptcy process on behalf of what they refer to as a stocking horse, you know, partner. So that's who the private equity showed up being. What, what that's to do is basically cleans up the balance sheet, you know, all those things, uh, resolves the debts and encumbrances. And I stayed on for about 12 months, roughly helping this new ownership group operate a business. Um, they had been in our industry. They had owned a couple companies that were ancillary to what we did. And so, um, but they didn't know exactly what we did and how we were doing it. So…

AI assessment note: “My family lost the ownership. All the employees were made whole and complete.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q you'll enjoy Sherry. She's very interesting. Let's get to the show. You've had a long career. And from what I understand, it's been mostly positive. I'm curious to know what got you into this industry, into engineering, you know, people call this STEM, right? What, what got you into a STEM career to begin with? Was it someone in your family? That excited you? Was it a teacher, a mentor?

A I would say all of those in particular. When I was around seven or eight, my father started taking an international correspondence course. He was an operating engineer. He wanted to become an electrical engineer. So this was not an online course. It was before then. It was a paper that you received a booklet, you worked through it, then you sent it back in the mail. It was graded. They sent you back the results plus another booklet. So I started working through those booklets with my father, and a lot of it was math. So, um, this is probably second grade I was in. I grew up in Ohio, and so by fifth grade, they do these international standardized tests, and I scored 10th grade in math. At that time. And one of my, my teachers shared that information with me, which have just encouraged me. And then when I went to junior high and high school, I had all women math teachers, which was unusual. And they all encouraged me to continue to study in mathematics. And that was, uh, what happened all the way up to university. I started the university and I said, oh, what am I going to do with mathematics? Oh, I'll be, I'll be an accountant. So I start studying accounting at the University of Miami, Miami of Ohio, and I was interviewing for some reason. I also thought I could be a journalist. I was interviewing the president of the university, maybe like the second week of the university, and…

AI assessment note: “I would say all of those in particular. When I was around seven or eight”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Exactly. So you had mentioned to me off air, you wanted to talk about investing, especially women investing in other women. So What is your particular message around that? What's your philosophy around it and all that?

A In the U S and in Canada, it's two to four percent of VC capital goes to women founded companies. One time it was a little more, we're talking about, you know, two trillion, you know, trillion dollars of, 450 trillion dollars of, of VC capital available. So, you know, I, I just finished a raise, uh, for my company, profound impact. We raised over three million dollars. Our target was three. We raised 3.1 to five million. Uh, so we were oversubscribed. So I was very happy about that, but I had to go to, uh, not the traditional. Angel investors. Now this is a pre-seed. We're not talking to VCs, but we are talking to a lot of men, and it turned out that I couldn't get, I mean, I did get some male investors, but what I found out was there was an untapped group of women, especially women who, who have wealth and, and are, they're philanthropic. Many of them have somebody else managed. Most of them have somebody else manage their money for them, the family office or wherever. However, they have never angel invested. So I tapped into that stream of women who have wealth, who are interested in this. They don't take all of their wealth. They take a small percentage and they invest in a company like mine, a women founded company. And it turns out there's a new article that I just read in the last few days from the 51 out of Calgary, uh, in Canada, that if we could tap in, if men would, i…

AI assessment note: “if women would invest like men invest, In angel and funds, that's over 3.22 trillion”

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