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  • keyboard_arrow_right How To Build A Multi-Million Dollar Exit Company Like A BOSS with Greg Shepard(BOSS Methodology) | Ep. 38


How To Build A Multi-Million Dollar Exit Company Like A BOSS with Greg Shepard(BOSS Methodology) | Ep. 38

Filip Stankovski April 6, 2020 1

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We all make mistakes as entrepreneurs but sometimes even with all of the information and courses don’t make things right. If you listen to our podcast with Greg Shepard, you’ll hear all about your mistakes in rolling up companies straight from the horses’ mouth.

Greg Shepard is the CEO and founder of BOSS Capital Partners. He is a Serial Entrepreneur, Author, Speaker and Angel Venture Capital Investor with a legacy of building and running sustainable growth businesses. Driven by a transformational leadership style, Greg has spearheaded multiple company exits in the BioTech, TransitTech, AdTech and MarTech space. Two of his former companies were acquired by eBay Enterprise Marketing Solutions in January 2016 as a part of a cross-brand deal totaling largely over $900M. The transaction comprised the purchase and sale of numerous companies, two of which were Greg’s.

If you’re interested in knowing how to build a multi-million dollar exit company using Greg Shepard’s BOSS Methodology, keep on scrolling down.

Remotrepreneur’s Insights:

  • Recognizing The Type of Business – Greg says it’s important to find out what type of business you want to target. There are two types of businesses – problem solving business and opportunity businesses. We break down what those are on our podcast.
  • The BOSS System – Greg also breaks down his famous BOSS system and passes the knowledge onto other entrepreneurs in need. The system is so good, Greg used it for politics as well.
  • How To Better Manage Businesses Remotely – There are a few things that make us distracted even when we work from home. Greg tells us how he manages multiple companies from any remote location.
  • BOSS Methodology in nutshell – Business, Operating, Support, System

The reason why I have been able to create 12 start-ups in a relatively short amount of time is because I built them to the point where they run themselves

Key Podcast Milestone:

03:24 – Greg’s story from living in a tent to building a billion-dollar company

08:04 – What does BOSS stands for

11:12 – First stage of Greg’s BOSS system

13:25 – Second stage of Greg’s BOSS system

28:20 – How to achieve the highest impact with the lowest effort

29:00 – Greg’s RACI model 

31:29 – Stage three of Greg’s BOSS system

33:13 – Stage four of Greg’s BOSS system

36:31 – How Greg makes people follow the SOP

37:15 – Last step in Greg’s BOSS system

41:30 – How many years it took Greg to develop the BOSS system

44:19 – The recipe for failure

47:53 – Why would people sell their company if it’s profitable

50:21 – The revenue tech companies need to make in order to be sold at a higher rate

59:34 – Greg’s best practices for operating remote companies

01:04:58 – Greg’s prediction and thoughts on the current economy

Top Key Quotes

“What you have to do is you have to change your strategy from becoming a victim to somebody who is taking the advantage of the opportunity”

“There are businesses that solve a problem and businesses that take advantage of an opportunity. Problem solving business – save money.  Opportunity businesses – make money.”

“Lower your expectations down to something that’s real and stop thinking about the exit price. That’s because when you go to build a business, you have to raise capital and when you’re raising capital, you’re selling a part of your business. The more you want to sell your business, the more capital you have to raise. You get into a circle and you say “I want to make 10 million off my business and I have to sell it at that point 25 million”. So, now you do a round of funding for 2,5 million. At a 30 million cap, you have to carry your businesses revenue numbers even further in order for the investors to get 2 to 5 exit on the investment”

“Businesses sell based on three value drivers – growth (which tells the buyer that the people are interest in your product, this is where you make sure your ICP and their ICP are aligned), the second thing – margin (margin says you could do it in profit) and the third one is – retention (retention says that your customers who buy from you keep coming back). Those three things are the most valuable things in the business”

“Now you have a list of things that you want to accomplish. But you can’t just stop there, you have to prioritize the list. Not all of those items are created equal. You have to break it down. You start with what’s important and what’s urgent. Something important prevents something urgent from happening. The urgent thing is the canary in the mine. If you have urgent things, you didn’t do the important things.” 

“You have your North Star in the beginning that tells you what direction you’re going in. Then, you break down your mission objectives and results, for each of those four areas. Now, you got into those four areas, you develop a prioritization system using urgent and important, impact and effort. Then, you delegate using the RACI model. Now, you’re ready to execute.”

“I start my day by setting up my intentions. Email is the tool, it’s not your boss, it’s not dictating what you should be doing throughout the day. It’s a tool that you control. So, I set my intentions first and I have a list and I say my missions and objectives. I look at those things and I make sure that I’m focused. I use email as an asset to accomplish what I have on my missions and objectives list.”



Jim Rohn


Meet the BOSS – The Agile Playbook for Startups – Greg’s upcoming book


https://www.gregoryshepard.com/ – Greg’s website


Greg Shepard – Greg’s Linkedin account

Greg Shepard


Don’t forget to get even more great episodes and resources to help you break out of the Matrix and grow your own remote empire at the Remotepreneurs website.

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Filip Stankovski

I'm a top rated sales freelancer on Upwork and Level 2 Seller on Fiverr. I believe that the new entrepreneurs are remotepreneurs and the purpose of the podcast is to teach people how to adjust to the new future of doing business - REMOTELY!

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