Fertilizer Fuels the HIGH Energy of the DigSouth (Virtual) Startup Conference

Last week the fine people of DigSouth in Charleston, South Carolina pulled off the impossible as one of the four best startup conferences in the South. They kept the high energy of the great opening keynote speaker throughout a full two day virtual conference, which is extremely difficult. Stanfield Gray and his partner and wife Sunny Gray deserve a champagne or craft beer toast from their Old North State neighbors. 

I would encourage you to become a member of DigNation and get to know why Time Magazine named Stanfield as one of the top people changing the South. I participated in the event to support Wilmington entrepreneur Derek Schmidt of SWELL Systems and WALE Angel Network client Tom Rump of Mesur.io in the Wild Pitch, which was better than Dr. Fauci and that “Just a bit outside” first pitch on Opening Day of baseball. (Tip of the cap sir but stick to science as I am begging for that vaccine so we can get back to hosting in person events again.)

Using the Shit Show in 2020 as Fertilizer for Growth

One of my new favorite people is Cassandra Worthy, who also spoke in 2019. I love people who can deliver valuable information but with a smile, a four letter word sense of humor and the high energy level to keep the attention of the ADHD entrepreneurs and creatives in the crowd. After a career with Procter and Gamble in consumer products, she is now the founder of Change Enthusiasm based in Atlanta. This year the conference partnered Cassandra with local hipster and small business owner of Sightsee Cafe and Retail bar Joel Sadler who moderated and narrated this opening keynote chat. This virtual “Screen Side Chat” covered a range of topics including how to personally embrace change in the work environment and managing your emotions and energy as fuel to strive in a time of turmoil.

Cassandra had the best quote of the conference, “If 2020 is the Shit Show, let it be the fertilizer for growth. “ Or if you are reading this and suddenly clutching your pearls, use this strange time to change the broken and pivot to get yourself right to move forward in the productive and positive lane. She took her own advice in this pandemic as she has increased her knowledge of technology products to advise her clients in a virtual environment instead of her usual travel schedule through airports to visit clients.

According to Cassandra, change requires recognizing the signals of fear and anxiety, to recognize and step into the new opportunity for learning and growth and then make the productive choice of which option to take. 


Use This Time to Transform

The VERY next speaker was an eye opening speech from a “new to me “ executive, Jeff Hilimire of Dragon Army, who is also known as a podcaster and the author of The 5 Day Turnaround: Lead like an Entrepreneur. Jeff spoke in stories to communicate about each of the five tips. To continue our theme, when the fertilizer hits the fan, entrepreneurs and leaders must:

Have a Do or Die Mindset – The thought of going ALL in to dedicate your full self to the business or you won’t give 100% and the back up plan creeps into your mind. The leader needs to think there is no other option but success.

Live your PVTV – Purpose Vision Tenets Values – These four beliefs must come from the top and embraced to the core by everyone in the company.

Trust in the Right People – As the company grows, there is a bigger chance that toxic people can get in and change the direction when you need people rowing the boat in the same direction. Positive changes after eliminating the toxicity led to an acquisition.

Move at the Speed of a Startup – After he sold his companies, he created an organization that created 48 web sites in 48 hours to help non profits in the Atlanta market. It was just enough of a CRAZY idea to challenge local creative people enough that they joined the event.

Welcome Failure – If you are not failing, you are being too conservative and cautious. He also talked about some companies that embraced failure by creating an award for taking the biggest risk that did not crash the company.


The Thorns of Public Relations

Entrepreneurs make lots of mistakes but public relations errors can be prevented before those mistakes become fatal. Rose Levy of Pace Public Relations gave some helpful tips since these earned media articles have ten to fifty times more conversions than paid advertising. You really need to match your great startup idea with a positive public relations (PR) strategy. Right now is an incredibly tough time to get out positive news about your startup if the news is not about the pandemic, the protests or the elections. Your company branding really needs to set you apart from a busy competitive industry to become top of mind. When you are reaching out to the media outlets, you need to research the appropriate form and channel of media, and communicate your unique features while being persistent and friendly with the reporter because they are currently overwhelmed with a 6-1 ratio of PR pros to journalists.


Choices Among the Warriors to Follow and These Two Warriors are Fierce Females

A common problem at big conferences is that there are multiple options among concurrent sessions and there is only one of you. But DigSouth was recorded and each session is available for view for the next 90 days. You should still buy a ticket even after the event, it was that good.

We all love to hear from people from the promised land of Silicon Valley so DigSouth delivered Promise Phelan, the author of The Growth Warriors about scaling your business with the Seven principles that she has learned in her career. From leading with empathy to being more flexible with the need to pivot and working in teams through collaboration with new affordable talent like freelancers. All of these things require that you take time to decompress and think since you are not stuck in traffic as much on I-40.


The final keynote that really got my attention before the pitch contest was Heather Hansen, author of the Elegant Warrior book and podcast. I have been looking for a way to encourage more “intellectual curiosity” in the Wilmington ecosystem so the entrepreneurs feel free to ask more questions and not just accept information from unreliable sources. Heather advised to promote the ability for younger people to be wrong without repercussions when asking questions within the leadership structure which requires trust. Heather also worked through an explanation of how to be a better advocate for the causes or people that you believe in. 

She gave a great opening statement to get the attention of the audience, “Facts Tell, Stories Sell but Advocacy WINS.”

Advocate > Communicate through the 5 C’s 

  • Connection
  • Compassion
  • Creativity
  • Curiosity
  • Credibility leads to confidence in your advocacy.

I hope you will welcome Heather to North Carolina when she relocates soon. And you know she is nice because she has already recorded her episode on my 3 Sips of Advice video podcast and we only met virtually on Friday! Much faster than a few of my friends followed up on the podcast request… no names but you know who you are.



The next big startup event in the South is 36/86 from Nashville next month and is a TEN DAY LONG EVENT but is very affordable as a $60 for the full conference experience and each day is sorted by an industry vertical. To finish the previously mentioned list of the big four startup conferences in the South include of course CED Venture Connect and the Venture Atlanta in October. Soon I may need to add the Tom Tom event in Spring in Charlottesville, Virginia.

These virtual events may not be the same as traditional ones but they are certainly more affordable since they don’t have to feed you, rent a big conference room, you don’t have to fly or get a hotel room and no one needs to know if you have Bailey’s or Kahlua in your coffee mug.


Jim Roberts is the Founder of the Network for Entrepreneurs in Wilmington (NEW), Wlmington Angels for Local Entrepreneurs (WALE), the 3 Sips of Advice video podcast, and 91omg.biz for local startup news at the North Carolina beach. He has built entrepreneur support organizations in Charlotte, Asheville, Durham and Wilmington over the last 20 years. You can follow Jim on Twitter @RedSpireUSNC or NEW on Facebook at @newILM.