137: Jimmy Hendricks (Lee Labs / Agency Maestro)

Jimmy Hendricks on Innovation City

A good team member is not going to join an idea that doesn’t have traction. A good idea solves everything. – Jimmy Hendricks

Welcome to Season 3 of Innovation City, a podcast featuring innovators, creators, and disruptors to discover how business is changing in the modern world.

Created and produced by SLAM! Agency in cooperation with Venture Café St. Louis and Venture Café Miami, Innovation City gives you an inside look at how rapidly business and culture are changing thanks to increasing diversity and inclusion, heightened creativity, and a stronger and better-connected business community. Venture Café is the largest combined gathering of entrepreneurs and innovators anywhere in the world. Events are held every Thursday in St. Louis, Miami, and other leading innovation cities around the globe.

Today’s guest is Jimmy Hendricks, General Manager of Lee Labs and Founder of Agency Maestro. Lee Labs is the technology venture group of Lee Enterprises. Lee Enterprises is a leading provider of local news, information and advertising in 50 markets across 21 states. His newest venture, Agency Maestro, is a SAAS platform designed to help any type of agency to manage their clients, track client work, store documents, and assets, create invoices, and bill their clients. Jimmy sits down with the Innovation City team to discuss his entrepreneurial background and journey, St. Louis’ busy and growing entrepreneurial ecosystem, the importance of raising capital after you’ve proven traction, his 2 biggest takeaways from his career thus far, and much more.

They discuss:

• His drive to be an entrepreneur has always been the element of freedom
• Most entrepreneurs will make money, but it’s usually not until the 3rd, 4th, or 5th+ try
• His first startup was in fashion and creating cool shirts that people could vote on, online
  • While it didn’t make much money, it was a memorable experience and jump started his career in entrepreneurship
• His second startup was a software platforms built to compete with Groupon
  • This is was first largely successful startup that garnered a multitude of clients, revenue, and venture capital
• Originally from St. Louis and studied accounting at Mizzou
• His connection with his current job at Lee Labs was formed after he sold software to them
• One of the most powerful lessons he learned was figuring out what he didn’t want to do
• The huge difference between St. Louis when left in 2004 and when he returned in 2018
• St. Louis’ busy and growing entrepreneurial ecosystem
• Helping Venture Café start Venture School
  • Venture School is a 12-week program for people who want to do SASS or online reporting
• There are many more tools today for entrepreneurs trying to build their prototypes and marketing than there were a few years ago
• The importance of raising capital after you’ve proven traction
• Understanding that a good team for your startup will come after you’ve proven traction
• Teaching a way to think, not what to think when mentoring others
• To find product-market fit, all you need a 1 page website and the charisma to go out and ask people if they think it’s a good idea
• A big reason agencies go under is because clients don’t pay
• His 2 biggest takeaways from his entrepreneurial career:
  • Self-funding to a certain point
  • Making sure you have a product-market fit
• Connect with Jimmy via email, LinkedIn, and Instagram

Lightning round:

• What is one of your favorite books?
  • Relentless: From Good to Great to Unstoppable by Tim Grover*
    • *Note that in the episode recording Jimmy mentions a book titled “Grit,” which he has since noted was incorrect.
• What’s the first thing you do in the morning?
  • Make sure he doesn’t have any meetings
  • Spends the first 15 minutes of his morning offline
• What’s the kindest thing anyone has ever done for you?
  • Early on in his first business, his step-father gave him 2 angel checks
• What is your superpower?
  • Optimism and connecting with people when they’re stressed out