10/26 Voices of Entrepreneurship: Glenn Clayton Recap

On October 26, 2022 the C4E hosted the second Voices of Entrepreneurship speaker series. Featured guest Glenn Clayton joined the C4E in person to discuss topics around entrepreneurship and venture capital.  

About Glenn 

Glenn Clayton is the managing partner of Mark Two Ventures, located here in Nashville. Before founding Mark Two Ventures, Glenn launched and scaled several ventures, including his first startup, Appleton, which he started out of his dorm room. He’s raised over 35 million in early-stage capital for his own companies, including one of Alabama’s largest series A rounds of venture capital. He has also successfully exited a company and scaled up another to profitability with over 40 million in ARR. 

Starting at the Beginning  

Glenn kicked the event off with his path to entrepreneurship. He confessed he did not plan to be an entrepreneur; in fact, he was a physics major in college with a love for science. His “broke college kid” intuition took over in order to make a few extra bucks to pay for his college textbooks. Glenn had been a tutor all through high school. By the time he reached college, he had a large enough network to match tutors to those who needed tutoring and his friends nicknamed him the “tutor pimp.” He realized the services he was providing to his college friend could be useful to a larger market – and make him some money! – so he started Appleton, a platform to connect parents to tutors. He began with no business plan, no intention to make Appleton a big company, and no capital. As time passed, he fell in love with solving problems and discovered his passion for entrepreneurship. He went on to sell Appleton in 2013, nine years after its launch in 2004.  

 The Other Side of the Table 

Pre-Covid, Glenn spent a couple of years as part of the talent-dense New York City start-up community. After moving back South to Tennessee, he began advising and angel investing in South-East ventures. He noticed founders coming to him left and right for help and advice on their businesses. Fewer people in the South-East region had gone through the startup process than Glenn was accustomed to in New York, and consequently, there were fewer advisors and investors to choose from in the region. As a southern native, Glenn wanted to change this dynamic. Glenn and his co-founder both had experience building multiple companies, robust networks of talented people, relationships with other large Venture funds, and were both angel investors. Mark Two Venture Studios was a way to bring all their resources together to help South-East founders access talent and build their companies correctly.  

At Mark Two Ventures, Glenn and his co-founder work with start-ups from the very beginning – idea-on-a-napkin beginning. The two look for ideas with no product, no revenue, no company so the studio can come in and co-found the new business alongside the entrepreneur. He had difficulty summing up everything he looks for in a founder. Still, he described that person as the one coordinating everyone, getting everyone motivated, and just caring about getting the job done. Everything else is teachable, but passion for solving the problem cannot be trained.   

The studio takes a methodical and precise approach with its ventures, adapted from Lean Product by Dan Olson. They begin with the ideation process, where market validation and MVP hypothesis testing occur. Glenn advised all founders to take a lean approach in this stage of their startup to avoid risk. “Too much money early on can hide a lot of weaknesses in your product,” Glenn said. He suggested waiting until you have market validation before raising large sums of capital.   

Ask Glenn 

Throughout the event, audience members were encouraged to ask Glenn questions to spark the conversation. Glenn advised the audience on several entrepreneurial topics, including: 

Seeking Out Mentors and Advisors   

Glenn touched on the importance of mentorship when launching your first startup. Mentors and advisors have been in the first-time-entrepreneur shoes before; they understand the process, and they can oftentimes help shorten the learning curve. When seeking mentorship Glenn suggests being candid and upfront. Tell them exactly what you are looking for, and often, people are willing to give you their time.  

Dealing with Imposter Syndrome 

The pesky cold entrepreneurs just cannot seem to get over – imposter syndrome. Glenn took a unique approach to deal with imposter syndrome. He argued it was actually a good thing. If you are building a company, you are trying to accomplish something that has not been done before. Having doubts about that is healthy. If you do not have much self-doubt, you are probably missing something.  

Hiring for a Startup 

Smart, hungry, and humble – that is how Glenn described what founders should look for when they are hiring.  

Smart – New hires do not have to be book smart, but they need to be smart about solving problems 

Hungry – No matter what a new hire’s goal is, they should have one. Hire people with ambition who are actively pursuing a goal. They will work hard to achieve it, and the startup will benefit in return.  

Humble – Nothing ever works at a start-up like it is supposed to, something is always broken, and there is always something to complain about. Founders need people on their team to encourage others when things do not work and lift up the team instead of complaining and blaming.    

Avoiding Confirmation Bias   

Now being on both the founder and funder side, Glenn has identified the fatal flaw of a founder – confirmation bias. He has seen time and time again founders get too married to the solution of a problem. “When you’re married to an idea, and you’re so convinced that you’ve got this amazing idea, you start looking for reasons to validate that you’re right,” Glenn said. Instead, he suggests becoming really obsessed with solving a problem and then figuring out how to solve the problem best. This mindset makes it easier to figure out where you, as a founder, need to be in the process and positions you well to critically evaluate whether the idea is worth your time for the next three to five years.  


The Voices of Entrepreneurship speaker series occurs once a month, with a new speaker from the entrepreneurial community each time. Make sure to subscribe to our newsletter to stay up to date on who will be speaking next. We hope to see you there! 


Watch the full Event: