From Side Hustles to CEO at 21: 3 Lessons on Sales Grit, Smart Automation, and Building a Self-Managing Business

Michael sits down with Jayson Miletta, a 21-year-old recent graduate of Rowan University and already a seasoned entrepreneur. Jayson shares how he turned a backyard cornhole league into a national franchise, launched a digital marketing firm with automated outreach systems, and built a scalable business model rooted in partnership and performance. This conversation covers the evolution of Jayson’s ventures, the systems behind his success, and his vision for the future—all before graduating college.

Tune into this episode to also learn:

• How Jayson scaled a cornhole league into a national franchise model.
• What it takes to cold-sell $100,000 franchises as a teenager.
• The difference between marketing “leads” and real business growth.
• How automation and AI are revolutionizing client acquisition.

What we discussed

[00:00:00] Jayson shares how he knew he wanted to be an entrepreneur after realizing basketball wouldn’t be his career path.

[00:03:57] Founding a national cornhole league and learning sales through trial and error.

 [00:05:40] Jayson describes using Facebook Lamborghini groups for cold outreach—learning from 10,000 rejections.

[00:06:49] Launching Jersey Jays Cornhole and expanding into fundraisers with a mobile tournament model.

[00:10:02] His earliest ventures: flipping Silly Bands in kindergarten and starting a clothing brand in middle school.

[00:12:31] How he pivoted from web design to performance marketing and the launch of GDG Media.

[00:14:38] Transitioning to a rev-share business model that aligns agency success with client growth.

[00:16:19] Why most agencies fail by selling “leads” and how GDG measures success by revenue impact.

[00:18:24] Expanding into verticals like credit card processing to drive more value.

[00:22:22] How Jayson uses AI to automate email outreach and schedule meetings without manual input.

[00:24:49] Leveraging massive proprietary databases to target ideal customers for marketing campaigns.

[00:26:15] Jayson’s five-year vision: location flexibility, consulting, and continuous growth.

3 Things To Remember

1. Starting early allows more room for trial, failure, and ultimately faster growth.
2. Systems, automation, and mentorship are key to scaling a business while reducing stress.
3. Business models aligned with client success—like rev share—create long-term partnerships and impact.

Memorable moments: 

(00:05:07) “I even went as far as joining Lamborghini owners on Facebook groups… and tried to message them because I had to figure it out.”

(00:14:38) “You can’t take leads to the bank… our motto is to track revenue and become a growth partner, not just a vendor.”

(00:22:54) “We actually only create female profiles—they get a 50% better response rate.”

Useful Links

Connect with Michael Pallozzi: https://www.linkedin.com/in/michaelpallozzihfm/

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