Entrepreneurship Podcast post

Business Science with Gregory Shepard

George Grombacher March 30, 2023

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Business Science with Gregory Shepard

LifeBlood: We talked about business science, what it takes for companies to become successful, why so many startups fail, an operating system that is effective, and the importance of pattern recognition, with Gregory Shepard, Founder and CEO of BOSS Capital Partners, serial entrepreneur, investor, Forbes author and podcaster. Listen to learn the five critical characteristics of successful entrepreneurs!

You can learn more about Gregory at GregoryShepard.com, Twitter, Facebook and LinkedIn.

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Our Guests

George Grombacher

Gregory Shepard

Episode Transcript

george grombacher 0:02
Well, Michael is George G. And the time is right. Welcome. Today’s guest strong and powerful Gregory Shepard. Gregory, are you ready to do this?

Gregory Shepard 0:08
I am ready. Thank you.

george grombacher 0:10
Let’s go. Gregory is the co founder of boss Capital Partners. He’s the creator of boss and open source operating system and powering entrepreneurs success rate. He’s the founder of boss startup Science Academy. He’s a Forbes contributor, a podcast host and author, and angel investor. Gregory, excited to have you back on the show. Tell us a little bit your personal lives more about your work, why you do what you do?

Gregory Shepard 0:35
Sure, I mean, so where it started was, I came from a family of, you know, a mixed bag of foster and adopted different different nationalities. And then I have autism and dyslexia. So I struggled, barely graduated from high school, and then I started businesses. And fast forward, I built and sold 12 companies and I sold a couple to eBay when for private equity awards for transactions between 250 and a billion as part of this $925 million dollar transaction. And then we I after I stayed with them for a little while I left and then I went into politics, because I was trying to give back, you know, I was trying to trying to contribute to specifically marginalized folks. So people that are trying to get out from check to check living, and I found out the majority of those people do it through starting a business, but then 92% of them fail. So I left politics, and then I went into this, and I was like, Okay, let me study why, when and how founders were failing. And I learned, I did 1200 Well, now it’s more than I started this in 2016. So at that point, when I made the switch was was about three years ago, I had done 201 on one interviews with founders, investors and all that we looked at, I think about 10,000 different case studies and reports. I mean, there’s a tremendous amount of research that took years and cost me about a half a million dollars for the team and everything that went into it. What came out of that was that the founder are failing. The first and foremost thing that they were failing over was the fact that they didn’t understand where they were and where they were going. This was like the fundamental thing, right? So they just kind of go into it, and they don’t understand, you know, where they are in this lifecycle, where they’re going, and that determines everything, right? There are, there’s a difference between doing the right thing and doing things, right. And that is, in some cases, timing. And so that’s what I focused on was putting together, okay, here’s a lifecycle that tells you where you are and what you should be doing at that point. Then I started creating classes, we hired a bunch of pedagogy, PhDs to go out and produce all these really well produced classes to help founders understand the lifecycle and what they should be doing and down to the detail. And then we started adding in tools that allows them actually do the practice on they actually go in and do the courses and learn how to do valuation and all that sort of stuff. And that platform is now powers, a bunch of universities and a bunch of accelerators, some economic development, folks and different things like that. And then we started adding in all the rest of the stuff that founders need. So this is like invidious accelerator lists, non dilutive funding lists, different pieces of software, evaluation software and cap table management software, and so on and so forth. Because the next step after understanding what was where they are, and where they were going, is making it so that they weren’t all starting at the same command line. You know, they all go in and they go to search, and they start searching for things. So we wanted to pull the whole ecosystem and put it in one place to prevent them from failing for those two reasons, or at least eliminate the common reasons why they fail. Because all that makes sense.

george grombacher 4:14
It certainly it does make sense. So

Gregory Shepard 4:18
post that we we started working really hard on trying to make sure that we had everything that was found or focus, so just okay, sorry. There was a break there. So, we we tried to really make sure that we were focused on what we can give to the founders first. And so now we’re building out a profile that holds all the founders actual empirical information that they can share with an investor because pitch decks are an awful way to try to communicate your pitch your business because it’s limited to the pitch you can’t as an investor, you can’t dig in and see you know, any details on it etc, etc. So that’s what we’re building right now. My in terms of the book, I got a book deal with BenBella publishing, I’m pretty excited about that. That’s the book supposed to roll out towards the second half of this year, which is really exciting. I’ve got a few books to do with them. So that’s really exciting. And, you know, that’s the catch up on me. I’m excited to be here with you.

george grombacher 5:23
I love it. I had the opportunity to learn with lots of other people to read Ray Dalio, his book, Principles, and it’s just amazed with how thorough he was with everything. And just it was one thing after another, and it strikes me that your system is very similar to that you’ve left no stone unturned, you’ve documented you put it all together, how long did it take you to develop this? Obviously, you were starting companies and selling them and making deals. But how long did it take you to kind of put the structure together?

Gregory Shepard 5:59
I mean, the whole thing is like my life’s work. So you know, I’ve been building businesses for between 2025 years. So maybe more than 25 years. So it was a matter of me trying different operating systems. So you have everything from like lean, and Six Sigma, and for dx, and oh, GSM, and agile and Kanban, and so on and so forth. And so what I did is I tested every one of these methodologies at different points in companies, and then used the parts that I thought were the best out of the out of the different ways of doing things. And then align them up so that there are certain things that are done at certain times. So that the founders are using things that are tried and tested and worked really well. But at the right time, you know, like, six sigma is a standardization tool, you know, it creates standardization. And so it’s better for standardization phase of the lifecycle and optimization, which is basically getting rid of waste and building out from there. So I spent a lot of time on on those operating systems testing, trying it. So that and then the lifecycle itself, and then all of the pieces, you know, over 25 years, and a lot of it’s my life’s work, you know, this is sort of, I guess my last hurrah, if you will, like this is the last thing I’m gonna want to do.

george grombacher 7:20
Oh, come on, you’re still a very young man. So I think there’s still a lot of water to go into the bridge, Gregory?

Gregory Shepard 7:26
Well, I’m Yeah, I mean, I’ve tried retiring. I don’t even I’ve lost track, and never works for me. So and I’ve said that before, so maybe you’re right.

george grombacher 7:36
Who knows? Who knows? So I’m fascinated by you watch YouTube videos about kids that can do a Rubik’s Cube in like two seconds. And it strikes me you obviously, when you look at something you could figure it out. And that’s probably the most crude way that anybody’s ever described. Your skill set? How do you what what, what do you think you’re really good at?

Gregory Shepard 8:00
Well, according to my diagnosis, you know, with autism, I have Savant syndrome, which is like, you know, being a savant, I hate the word syndrome, because it makes it sound bad. But it gives me the ability to see my superpowers, basically, patterns. So, you know, I can look at like an ecosystem, like the first one, one of the ones I did was affiliate, where I saw the performance marketing system, but I saw it back when websites were just being built, and before Google and right about When Yahoo just started, and I was able to see the future of this by following the patterns that I think are going to be coming in the future. And that’s sort of like my superpower. So when I look at, like, the whole startup ecosystem, I mean, you know, the, the number, the average number across everything is 90%. Fail, right? So nine out of 10 failed. It’s been like that for 15 years. So it’s sort of like, I mean, this needs to be fixed, you know, on the other side, understanding why when and how is creates another pattern, which is like, you can see that you have this incubators or have to accelerator or depending on what they call each other, that it’s a mess, right? You have investors that are think that they understand what to do because from an investor’s perspective, in that lens is completely different from a founder. They’re giving instructions to founder saying, well, you should be doing this, you should be doing that. And that’s good from their perspective, but they’re not the founder in the business. So a lot of times they give advice that is, isn’t doesn’t take into consideration the different angles of the Rubik’s Cube just one side. So they’re trying to solve one side of the Rubik’s Cube. You can’t solve a Rubik’s cube that way. You have to do it from all sides at the same time. The corners don’t move in the center is the access. So you can’t look at it from one side, you ruin the whole Rubik’s cube if you keep doing that. And that’s what investors tend to do. And then you have mentors who are the same, right. And all these people, they add to the founders ability to do the right thing. But the founder needs to be the access in the center of the Rubik’s cube. And so the problem is, is that the founder themselves aren’t getting real experience from the base. And so that pattern showed me okay, we need to start by standardizing how everybody thinks and looks and reads and talks about the startup ecosystem, then now everybody’s speaking the same language, we can educate on those standards, right, and those educational process creates other standards. And now that you have a standard, now you can move forward and really solve the problem. Because like, normally, if you’re like out there, and you’re in a school, every school is teaching people the same thing. When people graduate, they all have the same thing. One of the things that we teach in startup science, is that if you are trying to build something, trying to build a functional area, or build a product, or whatever it is, and everything is the data is different from multiple different sources, because there’s no standard, every financial driver or metrics measurement model you’re using is flawed, because they’re all different. So they all have to be similar or exactly the same for you to measure them pound for pound. So that was the first step in this process. And that’s sort of what I was able to see is like, Okay, we got to standardize everything, and then we can start measuring it, and then we can start making improvements.

george grombacher 11:44
Got it? I love it. How has how is the writing part Benton that come easy as well? Or?

Gregory Shepard 11:55
Yeah, so I mean, you know, I have level five dyslexia, right. So I read and write it like a fourth grade level. So, you know, I use machines to help me dictation and speech and stuff like that. And I have some software, that helps too. But you know, when I look at, like, if you look at a word of a page of words, you know, you can sit there and read letter by letter, word by word, and the grammar, the punctuation and keep going. For me, the whole thing is like moving, okay, so imagine taking a sheet of paper and then jiggling it around. And sometimes part of the letter shows up, sometimes, the whole letter shows up, sometimes it’s like, blurred is really, really difficult. And so, the writing, I mean, I’ve written like, 100, whatever articles, and, you know, I’ve done a TED talk, I’ve done all these different things, everything that I require requires this academic process. And so I’ve done work arounds, but it’s still really slow. You know, I mean, the book has taken me three and a half years, to get it to the point where it’s where we can actually slated for, you know, Mark when it’s going to be on shelves, and it’s taken me, you know, editors and other writers, like I’ve write the whole thing out. But I need, like, there’s three steps, right, I write the whole thing out, and it’s like this, I needed to translate or, you know, somebody has to take what I wrote, and then turn it into something that somebody else can understand. Just because things are all mixed up, my wife really helps me with that. She understands she calls it Scragg she speaks Greg. So she, she does that and then or somebody else and then it goes to another writer who sort of puts it into a format and then another writer who makes it really sound amazing. So it’s, it’s not you know, in I found out I thought this was just me, but this is all writers do this. This is a process everybody does. It’s rare that you find a writer that does the entire book on their own, it’s like anything else you need a group of people to do it. So but for me, you know, it’s a little extra help. So the process is a struggle is hard. It takes it drains me you know, if I’m working on the book for like a day, at the end of the day, I can’t see straight you know, unless just trying to just try to maintain but I do find it really fun. I really like to put on my headphones and just grind away on stuff that I have or or you know, go out and study the research and then put together something and then so so part of the the superpower I have was looking at a big picture with a lot of little pieces and then creating something that is a series of shapes and colors and stuff because I have this thing called synesthesia which is where you see like shapes and colors and that basically means things to me. So I’m good at like shaping that out and forming it and then putting it into a book or putting into a business or whatever so I can take a mess. You and cleaned it up? You know?

george grombacher 15:03
I love it. So when you are looking to invest in a company, which I know that you do, what what? What are you looking for? Is there something that this guy or this gal just has to have an like that?

Gregory Shepard 15:22
Yeah, I mean, you know, the, the, here’s the thing about a startup, right is that the, the idea is an art. But building the business as a science, that’s why we call it startup science, right? Because it really is, there’s a sequential process of going through that you follow. There are, of course, in those in that scientific process, it takes creativity to find your way. So if you’re a scientist, and you’re trying to find a cure for something, you study all the research, and then you look into the details, and then you’ll have to draw conclusions and then come up with an answer. That part is creative also. So I look for people that have the ability to think with data, not think to create data, but think with data. So, you know, you find a lot of people that are really academic, and they’re sitting there and they’re like, Okay, well, I’m gonna study what’s there. And I’m going to do this and that. And that’s not what it takes, you don’t need an academic person, you need somebody that has the ability to take what academic people do, and then create ways to move forward or ways to go around and obstacle through it, or under it, or whatever. And ways to look at multiple different pieces to something and put them together. Like when you’re looking at a business, there is an alignment between the product and engineering people in the shared services, people in the service delivery people, you know, operations and the sales and marketing people, you can’t have one of these things marching to their own drum, they all need to be aligned, that takes a specific type of a person. So that’s one thing. The other thing is the ability to take a beating, right? Like, if you talk to somebody, they’re like, oh, yeah, I’m an only child. And they were raised in a privileged household, and they haven’t struggled anytime in their life, the chances of them fail of them succeeding is rare, because they’re not used to it, they’re used to winning, and you don’t win the first time in, in, in doing it, being a founder, you work constantly failing for what and when. And, you know, so you have to find somebody who has the grit to take a beating, and get through that and not fall down, you know, not tumbled to the ground, that they have the ability to really, you know, fall down, get up and keep going without losing any motivation, drive, or enthusiasm. That’s the second thing. The third thing I would say is somebody that has that understands time management and organization. These two things can be time together. But that one is the ability to organize a lot of different pieces of data. And the other one is to manage your time on how you address the things that you need to get done by in prioritize order. And the big caveat to that is the discipline to do it. Right. So, again, I look for people that you know, I pay attention, I’m like, What have you done, you know, and they’re like, Oh, I was on the Olympic swimming team. Okay, well, you got discipline, right. And, you know, I was a project manager, okay, you’ve got an organization, you know, I had a full boat of courses in school plus a job plus a does plus that plus that, okay, you have time management. And then you have a collection of sort of experience assets that you can utilize with a founder, that would be the third thing. The fourth thing is what I call the handful, and the handful is just five things. So five thing five fingers, focus, drive, enthusiasm, discipline, and optimism. You have to have the ability to focus, you have to have drive. Discipline comes in when your focus and your drive fails, right when, when you’re sitting there and you’re like, nothing’s working, then you just got to pull yourself up by your bootstraps and do it. Enthusiasm is important, because you can’t lead a team unless you’re enthusiastic about what you’re doing. You know, you you you just put everybody to sleep. So you have to be enthusiastic and optimism is root, right? Because if you don’t think that the outcome of what you’re working on is going to give you what you want, then you lose your optimism and everything falls apart. So I look for the handful as the fourth thing. And the fifth thing is the ability to be coachable. So the ability for me to, you know, talk to them and that they don’t get defensive. You know that they can sit there and they can have me say, you know, no, do it this way. Don’t do that. This idea was bad. Whatever. In a pretty brutal way, because you know, with autism comes some pretty candid language. And so I’m pretty Can’t you know real honest with them, and just tell them straight up. And, and that is critical. And everybody thinks coachability is a big deal. So it’s not just me. And that’s the five things I look for.

george grombacher 20:19
I love it. Those make those make a ton of sense. Well, Gregory, grateful for you coming back on the show gratulations on everything. Where can people learn more about you? How can they? How can they take advantage of the boss operating system and the boss startup Science Academy? And keep an eye out for the book? All? Oh, thanks.

Gregory Shepard 20:40
Yeah. So Gregory shepherd.com says just grdg or YSHEP ard.com is my my website, and then start up. science.io is the website for the curriculum and all the other stuff. And I appreciate you having me on so much, George, I know you have like, tons of people lined up and I just appreciate that I was even considered. So thank you so much. I feel I feel very fortunate. So I appreciate it.

george grombacher 21:09
Yeah. Well, thank Thank you, sir. Have you enjoyed as much as I did show Gregory appreciation and share today’s show with a friend who also appreciates good ideas, go to Gregory shepherd.com. It’s Gregory S H E pard.com. And then go to startup science.io. And if you are a current entrepreneur or an aspiring entrepreneur, just entrepreneurial, curious whatever it might be, it’s clear that Gregory has done the work and recognize the patterns and taken the best of breed and all these wonderful ideas from lots of different places and distilled it down into into an actionable system that can help you figure out where you are and where you want to go and hopefully, be part of that 10% or increase that 10% to a larger number of people who are successful. So thanks again, Gregory. Thank you, and until next time, remember, do your part by doing your best

Transcribed by https://otter.ai

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