We caught up with the brilliant and insightful David Grubbs a few weeks ago and have shared our conversation below.
David, thanks for joining us, excited to have you contributing your stories and insights. Let’s kick things off with a hypothetical question – if it were up to you, what would you change about the school or education system to better prepare students for a more fulfilling life and career?
The educational system, particularly K-12 is in the middle of a large transition. Students are graduating from high school requiring a completely different set of skills than what was required when the current system was developed in the mid 1900s. Today students are entering a rapidly changing world with the likelihood of not only working for more than half a dozen different companies in their careers but also transitioning to several different industries.
We believe that students today not only require foundational knowledge that the current educational system provides but also intentional development of noncognitive skills like real-world critical thinking, problem solving, fortitude and grit, adaptability, perseverance, self-reliance, and opportunity identification.
While there will be multiple paths for schools to teach these skills, teaching entrepreneurship and incorporating entrepreneurial thinking into all classes is a proven way to develop these vital skills.
“Entrepreneurship refers to an individual’s ability to turn ideas into action. It includes creativity, innovation and risk taking, as well as the ability to plan and manage projects in order to achieve objectives. This supports everyone in day-to-day life at home and in society, makes employees more aware of the context of their work and better able to seize opportunities, and provides a foundation for entrepreneurs establishing a social or commercial activity.” (Commission of the European Communities, 2006: 4).
The Consortium for Entrepreneurship Education (2008) states that “entrepreneurship education is not just about teaching someone to run a business. It is also about encouraging creative thinking and promoting a strong sense of self-worth and empowerment. Through entrepreneurship education, students learn how to create business, but they also learn a lot more. The core knowledge created via entrepreneurship education includes:– – – – The ability to recognize opportunities in one’s life. The ability to pursue opportunities, by generating new ideas and found the needed recourses. The ability to create and operate a new firm. The ability to think in a creative and critical manner. So, beside knowledge and skills in business, entrepreneurship education is mainly about the development of certain beliefs, values and attitudes, with the aim to get students to really consider entrepreneurship as an attractive and valid alternative to paid employment or unemployment.” (Holmgren et al., 2004; Sánchez, 2010a).
Although not all youth will become entrepreneurs, all students and society benefit when individuals have a solid education, that gives them entrepreneurial knowledge and skills to use over their lifetime.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
I am a serial entrepreneur and have founded a dozen businesses in ecommerce, logistics, software, and consumer goods over the last 20 years. I have been blessed to be involved in three successful acquisitions of his businesses and generated over $50MM in combined online sales.
2011 through 2013 I had the opportunity to teach entrepreneurship at Baylor University as an adjunct lecturer for under the guidance of Dr. Kendal Artz and Dr. Les Palich which is the source of inspiration for my current venture, Boss Club (www.bossclub.com) which I cofounded with long time business partner Charlie Gasmire in 2018.
Boss Club provides entrepreneurship curriculum to over 200 private and public, middle and high schools across the US representing hundreds of teachers and thousands of students every year teaching and participating in the one or two semester program. The Boss Club curriculum provides a unique model that guides students through the process of launching a real business as part of this extra-curricular class in school and generates proven outcomes and results teaching financial literacy and key skills necessary for students to flourish in the world they are about to enter including (real-world problem solving, critical thinking, grit and perseverance, self-reliance, and identifying opportunities particularly in times of constraint).
We’d appreciate any insights you can share with us about selling a business.
I have sold three businesses over the past seven years and the process for doing that effectively starts months, if not years, before you start talking to potential buyers.
First, you need to define what your goal is with the acquisition. Why are you selling the business in the first place? Are you wanting the capital to start something new? To retire? To get out of the business because you are burned out? Knowing the answer to this is key.
If you have a business that is in a position to sell then you have already gone through the grueling task of building a profitable enterprise that is producing a return for you. That usually takes years and large returns are usually not seen until compounding interest/growth has time to take effect so why exit and start over?
Real value is brought to the business if you can set it up in such a way that it can operate largely autonomously and does not require all of your time and attention. If you can get the business to this point it will be much more valuable to a potential acquirer but it also becomes that much more valuable to you. The decision really then comes down to if you think you can sell the business and use that capital to generate a greater return than your current business. Alternatively, if you can keep the capital in the business and simply take dividends over time as it runs independent from you. If you keep the business but need capital for something new, you can leverage the business through debt and use the capital to invest elsewhere while retaining complete ownership of the original business.
The point is regardless of your decision of whether or not to sell, you want to get the business to a place where it can operate and grow without you. If you can do this then you will have many opportunities available to you including a solid foundation for acquisition or to retain the business as an asset long-term.
The actual mechanics of acquisition is somewhat tedious but I have always found that part to be relatively straight-forward. Find an entrepreneur that has done it successfully a few times and have them mentor you through the process.

Can you open up about how you funded your business?
Early in my career I raised funds the traditional route with friends & family money, followed by angel investment, etc. While it was a good learning experience, all of my businesses for the past decade have been self-funded and most were started for less than $50,000. The businesses I self-funded have been much more successful than anything investor backed.
I think boot-strapping until I had a proven and scalable sales model is key to helping me stay focused on the few key things in the business that truly mattered. It forced me to be creative and to solve problems with constraints which created efficiencies and a solid early foundation.
In my early businesses, the moment I raised funds from investors I was now an employee again working for a boss who expected a return on a certain time-horizon (usually 5-7 years) with an exit event. As an entrepreneur this changed my whole approach to building a business and not for the better. I was short sighted.
Today my co-founder and I own our business outright, we have the freedom to make long-term investments in product that we know will take ten years or more to play out but we also know that it is exactly those kinds of initiatives that can make a profound impact on the world and as a result make for a profitable and valuable company in the long-run. We can make solid long-term decisions without have the pressure of needing an exist in a few years and that makes all the difference in the world.
Raise money with caution.
Set yourself up where your business is a game where if you wait, you win. – Alex Hormozi
Contact Info:
- Website: https://bossclub.com/
- Instagram: https://www.instagram.com/bossclubco/
- Youtube: https://www.youtube.com/channel/UCrgkiOQBtLAwfmeTMOjwFfg
- Other: Podcast: https://www.buzzsprout.com/1845540

