enlighteninG & RELATABLE

"Greg immediately pulls listeners in with enthusiasm and keeps them listening by providing usable knowledge."

   -  Darin Andersen, Founder, Seamless Podcast

Featured On


  • Altruistic Capitalism

  • Start-up Failure Myth

  • Challenging the Status Quo

  • Helping Entrepreneurs

  • Believing in Yourself


  • Phase 1: North Star

  • Phase 2: Strategy

  • Phase 3: Execution 

  • Phase 4: Standardization

  • Phase 5: Kaizen


  • Level 1: Survival

  • Level 2: Documented

  • Level 3: Aligned

  • Level 4: Market Leading

  • Level 5: Predictable

CEO, BOSS Capital Partners, Greg Shepherd: Investing in Startups


"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."

Crisis Management Framework (Part 4): The bare essentials


"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."

Crisis Management Framework (Part 4): The bare essentials


"In continuation of the last week, this week, I would focus on additional areas to consider during the Crisis. I would highly recommend if you haven't listened to the first three episodes of Crisis Management Framework, then before you hear this episode, please do listen to the three parts."

Crisis Management Framework (Part 3): Standardization and Kaizen Loop


"In continuation of the last week, this week, Greg and I would focus on the Standardization and Kaizen Loop phase post Strategy and Execution phase."

Crisis Management Framework (Part 2): Strategy and Execution


"In continuation of the last week, this week, Greg and I would focus on the Strategy and Execution phase post definition of North Star. I would highly recommend if you haven't listened to the first episode of Crisis Management Framework, then before you hear this episode, please do listen to the first part. "

Crisis Management Framework (Part 1): Define your North Star


"The last three months have been roller coaster ride for the entire world. Economies and markets are planning to open up and trying their best to resort to normalcy. However, the last three months have changed how the world, individuals, and businesses have shifted their preferences, habits, needs, and wants. It is imperative that organizations relook at their priorities and how they look to drive their business ahead. "



"I am joined by Greg Shepard, CEO and founder of BOSS Capital Partners. He is a serial entrepreneur, author, speaker, and angel investor with a legacy of building and running sustainable growth businesses."

The How-To Entrepreneur: Greg Shepard


"Greg Shepard made a $900 Million Exit when his company was only 3 years old back in 2016. This was not a fluke, this was not luck... This was method, preparation, and execution! Greg shares what and how important a North Star is to have when creating your company and how you can align your actions with those coordinates in order to reach entrepreneur goals with his very own BOSS Method™"

The Game Changer: Why Isn't This Common Knowledge?!


"In this high impact series, you will be able to listen for 8-10 minutes and have an actionable takeaway to have a Money Talk with your kids. If you do this once a week for a year you will have 52 Money Talks to vastly impact your children's financial trajectory, improve your relationship and open the door to talk about Money, Entrepreneurship and Successful Mindsets for the rest of your lives."

Develop a North Star


"Throughout his decades of experience, Greg has found that there is one common denominator among businesses that fail—they lack a north star. According to Greg, a north star is like a roadmap allowing you to get from point A to point B. Without it, you'll never get to where you're headed."

How To Create An Exit Strategy For Your Business


"Starting a business is easy compared to exiting a business. Too many entrepreneurs get into business to make money but never give any thoughts to how they will exit the business. Will they sell it, leave it for family or simply close it down? What will happen to their income when they no longer have the business? These are the types of questions we will be asking Greg Shepard today from Boss Capital."

Best Business Strategies To Really Crush Your Profit


"Today our guest, Greg Shepard shares the framework and strategy for having a successful business. He also talks about the 12 different companies that he has developed and sold."



"Today, WTR welcomes Greg Shepard, serial entrepreneur, investor, Forbes author, and Ted X speaker. In this week’s episode, we discuss the steps that occur in the crisis journey, and how to get your business to return to deliberate operations."

Tea with Gabriel


"Greg is the creator of the BOSS Operating Support System. The BOSS Operating Support System is a strategic playbook that teaches entrepreneurs how to scale a business through a step-by-step guided process that covers every aspect of functional alignment, growth and scale."

angel investor Greg Shepard: Part II


"This is the second Episode of Splinter Business Stories with angel investor and entrepreneur Greg Shepard. Probably this is the most insightful conversation in the entire show. If you always wanted to realize your idea, plan investment, and learn about the  "backstage" of start-ups and finance, you are at the right place here and now. "

How to Grow Your Business Using a North Star


"This week Gregory Shephard, serial entrepreneur, angel investor and creator of the BOSS business operating system joins Allison Hartsoe in the Accelerator. Greg explains the BOSS methodology then shares the first part of his method: using a North Star to grow your business."

BOSS Crisis Management with Gregory Shepard


"During times of uncertainty it’s important to have a proven plan in place to navigate through choppy waters. Do you have a strategy in place? In this episode, Adam Torres and Gregory Shepard, Founder and CEO of BOSS Capital Partners, explore BOSS Crisis Management’s proven strategies. "

angel investor Greg Shepard: Part I


"The guest of today's episode of Splinter Business Stories is Greg Shepard, entrepreneur, author, and angel investor. His investment firm, BOSS Capital Partners, helps startups on their seed stage."

Surviving COVID-19


"Today we bring you two expert guests who, combined, have grown and sold close to $2 Billion worth of businesses. Learn how to manage and salvage your business during these tough times of COVID-19 and how you can keep your business afloat and come out stronger when it is all done!"

Special COVID-19 Episode: Survive This Crisis


"Randall LaVeau and Greg Shepard share valuable tips and ideas for guiding your business through the COVID-19 pandemic."



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

Gregory Shepard - The BOSS Framework


"Greg discusses his Business Operating Support System (BOSS) and how it can help entrepreneurs achieve a rapid and lucrative exit. "

Why Your Business Needs A Northstar


"Taking the time to think thoroughly to establish a company's North Star will fundamentally change the approach to starting a business, from the initial steps you take to get it off the ground to how you approach and prepare for the eventual exit. Greg Shepard explains this and more."

Leadership beyond borders


"Although statistics vary, most are showing that around 61% of Generation Z entering the workforce now, say they want to be entrepreneurs, and very few want to do it because of money. Being creative, solving a problem and making life more efficient top the reasons why. But being an entrepreneur is hard. With 8 out of 10 start-ups failing it would be not very easy to be a success without much experience and some sound advice. In this episode, we look at why start-ups fail, but more importantly, we reveal the secret formula that can help entrepreneurs succeed."

The TEch Blog WRiter Podcast


"Greg Shepard is a seasoned veteran in building and running sustainable growth businesses. His former company, AffiliateTraction, was acquired by eBay Enterprise Marketing Solutions in January 2016 as a part of a cross-brand deal totaling $985M.


Most recently, he has been authoring a book titled: ‘Meet the BOSS - The Agile Playbook for Startups slated to publish in Q4 of 2019. Alongside the book will be a TED talk.


A must listen for any startup founder."

Hustle Sold Separately


"Want to know how to rethink your goals so you can create something you know will be successful? Matt @mattgottesman sits down with Greg Shepard (Serial Entrepreneur, Angel Investor and Venture Capitalist) to talk about what really makes business goals successful, how the mainstream has it all backwards when it approaches building a brand, doing things with the best intentions in mind, setting others up for success has a ripple effect, the importance of nurturing talent and helping them throughout their journeys, taking the high road always, his streamlined BOSS approach to companies and more…"

Fuel For Startups


"Gene Swank is joined by special guest Greg Shepard, a serial angel investor and venture capitalist."

Seamless Podcast


"Darin and Grant speak with serial entrepreneur, Greg Shepard, who many call the “the King of the Affiliate Marketing”.  Greg is also a writer, speaker and tech angel investor.  Greg’s startup AffiliateTraction was purchased by eBay, where he is now the Chief Strategy Officer and CTO.  AfflilateTraction was rebranded as Pepperjam and is now a $1 Billion business comprised of the rollup of 14 companies, including AdAssured, another company founded by Greg."



Most people still don’t know what affiliate marketing is. Well today’s guest understood it so well that he created a business that would allow anyone to start an affiliate program.

Greg Shepard is the founder of AffiliateTraction (renamed Pepperjam) which is a multinational affiliate marketing agency and was acquired by eBay.

I want to find out why he thought of himself as a failure and why he actually might have been one for a while.

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