1617 – Gathering Specialists with Startup Science’s Gregory Shepard

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks to the Founder & CEO of BOSS Startup Science, Gregory Shepard.

According to Gregory, bad decisions are the number one reason for startup failure. However, he explains that bad advice is the root cause of these bad decisions. Surprisingly, the main contributors to lousy advice are investors and mentors. This is attributed to investors needing firsthand experience as founders and mentors needing to understand the specific needs of each business.

Investors may give advice based on their experience working with founders, but with a deep understanding of the operations and details of the business, their advice can be beneficial. For instance, they may push founders to raise money or focus on valuation without considering the long-term consequences. Similarly, mentors who have had success in the past may need more expertise to provide relevant and practical advice for current market conditions.

To address this issue, Gregory suggests a model similar to the medical field, where general practitioners refer patients to specialists for specific diagnoses and treatments. In the business world, it is essential to seek advice from specialists who deeply understand the particular challenges a founder is facing.

Shepherd emphasizes the importance of teaching founders the necessary skills and knowledge so that they can navigate their entrepreneurial journey independently. However, mentors are still valuable in providing context and guidance. For example, if a founder takes a course on valuation, they will understand how valuation works and be able to defend themselves to an investor. Conversely, mentors can help founders along this learning journey by understanding how they have learned valuation.


Key Points from the Episode:

  • Common reasons for startup failure
  • Bad decisions as the number one reason for failure
  • Investors and mentors as main contributors of bad advice
  • Lack of firsthand experience as founders and understanding of specific business needs
  • Importance of seeking advice from specialists
  • Resources and courses offered by Startup Science
  • Tools such as grant finder and investor network
  • Teaching founders necessary skills and knowledge
  • Openness to suggestions and advice from mentors and interested individuals


About Gregory Shepard:

Gregory is a highly experienced serial entrepreneur, having completed 14 liquidity events, including two notable transactions contributing to a $925M deal that won four PE awards for deals between $250M-$1B.

Known for his strategic insights, he's a ForbesBooks author with over 100 articles published in national and international outlets. Shepard is also a TEDx and keynote speaker at numerous universities, associations, and conferences globally.

As the host of Meet The BOSS on Forbes Radio, he shares his expertise widely and is a regular guest on popular podcasts, TV and radio shows. Co-founding BOSS Capital Partners, where he facilitates global investments in tech startups.

Moreover, through BOSSStartupScience, he provides entrepreneurs with resources and guidance via his Business Operating Support System (BOSS), an open source methodology designed to improve startup success rates.


About BOSS Startup Science:

BOSS Startup Science aims to improve the success rate of startups, given that the current 90% failure rate is disheartening. The CEO, Greg Shepard, believes that education, connections, and assistance are crucial to helping founders succeed.

Their mission is to support startups in achieving success, focusing on one founder at a time. This endeavor is fueled by the understanding that wealth inequality is closely tied to entrepreneurship, with 95% of people improving their financial situations by selling a business.

BOSS Startup Science began by extensively researching the reasons behind startup failures. They conducted 1,200 interviews and thoroughly analyzed research data. The findings revealed that many founders repeat avoidable mistakes, primarily related to people, knowledge, and financial resources.

While accelerators are designed to aid startups in overcoming these challenges, only 2% of applicants get accepted. The main reasons for rejection are needing more knowledge and connections within the startup ecosystem. Hence, BOSS Startup Science seeks to provide founders with the necessary tools, knowledge, and networking opportunities to increase their chances of success.


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Josh (00:00:05) - Hey there, thoughtful listener. Would you like consistent and predictable sales activity with no spam and no ads? I'll teach you step by step how to do this, particularly if you're an agency owner, consultant, coach or B2B service provider. What I teach has worked for me for more than 15 years and has helped me create more than $10 million in revenue. Just head to up my influence and watch my free class on how to create endless high ticket sales appointments. You can even chat with me live and I'll see and reply to your messages. Also, don't forget the thoughtful entrepreneur is always looking for guests. Go to up my influence and click on podcast. We'd love to have you. With us right now, Gregory Shepard. Gregory, you are the founder and CEO of Startup Science. You're found on the web at Startup Sience dot io. Gregory, thank you so much for joining us.

Gregory (00:01:10) - Thanks for having me.

Josh (00:01:11) - Boy, we had a great conversation. We were like, Man, we better start recording this stuff because we found like just so many common threads in our backgrounds and experiences.

Josh (00:01:19) - But. Gregory Give us an overview of what startup science is.

Gregory (00:01:24) - Startup science is a platform that is used to power universities, accelerators and other startup assistance programs, and it's built specifically to help founders get through the gauntlet of becoming successful. So it was on the heels of a five year study on why win and how founders fail. That started in 2016, and we found out the commonalities and sort of the trends and patterns that show founders are failing. Most of them fail for the same reasons over and over and over. So my goal was just to stop them from failing. For those reasons, they could fail for other ones, but not those reasons. And that's what we built.

Josh (00:02:01) - Well, you've certainly evoked my curiosity. What are some of the big reasons that founders fail?

Gregory (00:02:07) - The number one reason is bad decisions, but that is actually not the real reason, the real reason, the number. So if you look at it in a stack, right, there's the top of the tree, which is what everybody sees.

Gregory (00:02:18) - And then there's the roots underneath the ground. The top of the tree says bad decisions underneath the ground that splits off. And the number one reason out of those actually has to do with bad advice. They're making bad, bad decisions because they're getting bad advice. And the bad advice, the number one contributor of bad advice is actually investors. And the number two. Yeah. And the number two is mentors. So it's pretty interesting. You know what?

Josh (00:02:49) - I wonder what kind of bad advice that you hear or have heard of investors sharing, which this is surprising, right? You would think that, you know, someone that's putting their money in is going to be pretty deliberate, you know, and they're going to make sure that they've vetted whatever it is that they're recommending rather than just spouting off opinions that may or may not work. But what are some common pieces of bad advice that you might hear from an investor?

Gregory (00:03:16) - Yeah, it's not it's not that they don't they have the right intentions, but yes.

Josh (00:03:20) - Oh, sure.

Gregory (00:03:21) - Yeah. And there's a difference between the view of the world. Right. And investors looking through a lens that has to do with their experience working with founders, not being a founder. Almost every one of the investors that we went and did interviews with, which was about 2100 of them, had never been a founder before. So their advice was coming from them being an investor, working with and watching founders, and then relaying that as a third party to the founder. But every founder has a different journey and they're going through different things. And if you're an investor and you're just saying, listen, you need to go raise money, but you don't understand the operations and the details inside of the business, that's bad advice, right? Or the investor, a lot of the times will say, well, we need to raise the valuation. Well, why if you're working with a PE or venture capital, their business model is two and 22% of what they raise in 20% over the hurdle.

Gregory (00:04:18) - So 20% over how much they invested. Right. So their profit basically on the on the cap table. So they're motivated just like any other broker to fund more companies to get their 2% higher and to make their portfolio look bigger, which is based off valuation. So the number two problem in that bad decision stack is valuation overvaluation. So what's the evidence? We'll look at the market right now. Right? You have companies that have dropped in valuation by 50%. That's an over valuation problem, right? So it wasn't the founder that was doing that in most of the scenarios in the study. It was the investors telling them to do it or telling them take on money, take on money, take on money, which, you know, post money raises the valuation. So it's a systemic problem. And the investors need to either refrain from giving advice that they don't understand the depth of right. Or they need to rely on other resources that are willing to dig into the business enough to deal with you know, to give them good advice.

Gregory (00:05:31) - That's the big problem. The same thing happens with mentors, right? So you have the one hit wonder, right? Some cat that goes out, does business, is successful. And now I'm a mentor and I'm a successful mentor.

Josh (00:05:44) - And I put radio on the Internet.

Gregory (00:05:46) - Right? Yeah, exactly right. And then you have the ones who have done it maybe twice and you don't know, maybe they hit a trend that was coming in. The waves were already come in and they just happened to be standing there and got pushed to the shore. Or maybe they were out there paddling their ass off too early and, you know, waited for the wave to come in. Or maybe they got funded really well or mommy and daddy have money or, you know, you got some special scenario like Facebook where the market just happens to be all the stars are lined up and you get a win, right? So the advice that people give to founders needs to be catered towards what's going on in the market and what's going on in their business and the combination of understanding the operations of the business.

Gregory (00:06:27) - Otherwise it always leads to disaster. In fact, the numbers say that 51.7% of the founders fail within a year of leaving an accelerator or startup assistance programs. Those programs are meant to help them. So it makes you ask the question like, what are they doing with them? Right? So I studied those things to figure out like what was happening in that process and that that's what happened, right? Is them getting bad advice from a series of people and it may be the person they're getting advice from is somebody that's a vertical subject-matter expert, meaning that SME is somebody that understands pharmaceutics. Tickles or TAC or something like that. Maybe on the other side you have somebody that understands the vertical but doesn't understand sales and marketing. So it's a combination of understanding the industry they're in and the functional area that they're in as they go through the life cycle. So if you're an early stage founder and you have a vision, a vision and you're in the vision stage, your needs in terms of advice or drastically different than somebody that's in a growth stage, a standardization stage or go to market stage or product or whatever.

Gregory (00:07:39) - Does that make sense?

Josh (00:07:40) - Yeah, yeah, it's almost like that, you know, the way you're describing it to I'm thinking, you know, my brain's thinking about that. I forget what that fallacy is, alleged certainty or something like that, where it's like the more that someone insists that they have the answer right, the more that you should probably take that with a dose of skepticism. And in fact, you know, it's men of science and women of science who will say this is our best guess based on the current data. Right. And it's just a different tone. And that, to me, evokes so much more confidence because I know that, you know, there I feel like it's just more trustworthy, right? And, you know, similarly, I think, you know, another thing I respect from mentors, right, is this idea of, listen, I know this area well. Like for me, like I know one very niche, narrow thing and I'm probably one of the top ten on the planet at this one very niche narrow thing.

Josh (00:08:41) - 99.9999999% of the stuff I'm pretty unremarkable.

Gregory (00:08:46) - Yeah. And that's pretty typical for people right so what the model that I suggest mentors or founders use is the same model that you get in medicine, right? So when you go to a general practitioner, they don't start telling you about spinal stuff or kidney stuff or whatever. They send you to a specialist, right? So the general, the doctors these days are pretty much like project managers, right? You come in, you're like, I have this going on. Okay, go see this place over here, you know? And then that person does the special work that's associated with that particular diagnosis or gives the diagnosis. And the same thing applies for businesses, right? You can have one person who's an overall generalist, but you need to have somebody that says, I know how to do go to market and not just go to market. I know how to handle email, I know how to handle social, organic and pay to cross platforms, right? I know how to handle partnerships.

Gregory (00:09:42) - Whatever it is. There's a very special detailed understanding that you have to have in order to give good advice. So it's not that you don't want to give advice, you just want to give it. Don't get over your skis, you know, and the advice that you do give.

Josh (00:09:57) - Tell me more about how someone can take advantage of the resources that start up sciences or is this primarily just for organizations to connect with and make this available to their members? In other words, are there business leaders that can somehow partner with or connect with startup science to be involved in some way?

Gregory (00:10:18) - Yeah. So I have when I did the original study, I got a book deal with Denver Publishing, so there's a book coming out at the end of the month called Startup Science actually. And in conjunction with that, I launched a version of the platform on Gregory Shepard, which is my website specifically for founders, because I wrote about 5000 pages that I couldn't fit into the book. So the courses that are inside of there are built to help people get around the reasons why founders fail.

Gregory (00:10:50) - In fact, most of the courses start out with this percentage of founders fail for this reason. Here's how you don't fail and it's watched, listen, read and experience so they can actually do the work. In addition to that, there are tools so you can come in and there's a grant finder tool. We have 60,000 investors that we use to pair the founder up with investors. So it makes it, so you don't need as much of the advice that is reoccurring, right? Like if something is done over and over and over again, you don't need a person, you just teach somebody what that thing is, right? And that's what startup science has a lot. You can communicate with founders if you're a mentor or whatever, but it's meant to sort of give context for them. So you're taking a course on valuation. You understand how valuation works, so you can defend yourself to an investor, but your mentor also understands how you've learned valuation, so they can help you out with that journey. We're always looking for people who have suggestions and advice and, you know, mentors, everybody that is interested in working with founders.

Gregory (00:12:00) - So we add them into their into the system. And then the founders can choose from who they want to work. So it's I mean, to your point, anybody that is interested in working with founders, just go to Gregory Shepard. Com. Fill out the contact form and I'll work with you or somebody will but we'll get it you know we're a lot of the stuff that's in there has come from people on the outside saying, hey you don't have a course for this or you don't have a tool for this. Like one of them was, the most recent one was the ecosystem. So I preach to people, I'm like, you have to understand your ecosystem, which is made out of customers, partners, competitors and acquirers. Right? And it's really, really takes months to put together your ecosystem. So we built a tool that does the ecosystem for them in like a half a second. So that's like an example. So I'm into anything and everything that people want to send our way. That'll help founders.

Gregory (00:12:57) - The goal being help founders succeed.

Josh (00:12:59) - Yeah, The website again is Startup Silencio. What do they click on?

Gregory (00:13:04) - Visionaries.

Josh (00:13:06) - Visionary biz. Okay, good, good, good, good. Awesome. Well, listen, it's been a great conversation. Gregory Shepard I'm so grateful that we've crossed paths. Thank you so much for your contribution. I know you have a long and storied background, which we didn't even get into. You and I talked about that before we hit record, But here's what I would recommend. Gregory You're you do great LinkedIn. And so I think that if you search Gregory Shepard on LinkedIn also it should be linked up on the startup science. You'll get there as well through your company pages. By the way, there's a company page for startup science and then you'll find we'll find you. Yeah, you're a great person to follow on. On social, you produce, you share great stuff. So, Greg, I just want to say thank you so much for being a guest.

Josh (00:13:56) - And again, website startup science dot IO Gregory thanks for joining us.

Gregory (00:14:02) - Thank you. Take care.

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