Tom Mirabella left corporate at 30 and never looked back. Seventeen years later, he’s built Wingman into a 25-person business by doing what corporate rarely rewards: solving problems fast, betting on relationships, and staying obsessively close to customers.

In this conversation, Tom breaks down his escape story, why “local + in-person” is making a comeback, and how Wingman’s franchise model flips the typical franchise script — where the franchisee focuses on relationships and sales while the central team handles fulfillment and delivery.

If you’re stuck in corporate and can’t see a path out, this episode gives you a practical look at what “building your own lane” can really look like — without pretending it’s easy.

Join the Escapee Collective: TheEscapeeCollective.com

What You’ll Learn

• Why Tom left corporate early (and what corporate policies taught him about ceilings)

• The side-hustle-to-business path: how one small project turned into real clients

• How to think about risk when leaving: your monthly “number” vs. replacing a salary

• Why entrepreneurship can swing from best day to worst day in 30 minutes — and how to handle it

• The “digital mayor” concept: becoming the trusted local hub in your town

• Why Tom believes physical locations + community presence still win in a digital world

• A modern franchise approach: franchisee sells + builds relationships, HQ team delivers

• Why customer service and trust are the real differentiators in crowded markets

Key Quotes

• “The problem’s now. Two weeks from now, it’s worse.”

• “As an entrepreneur, you can have the best and worst day within a half hour.”

• “I want you to be the digital mayor of your town.”

• “If you do what you love, the money follows.”

Mentioned in This Episode

• COBRA and how Tom thought about early-stage risk

• Networking groups, chambers, community events, and “planting seeds”

• Using a podcast as a lead generator (and why it worked)

Connect with Tom

• Email: Tom at wingmanplanning.com

• Website: WingmanPlanning.com

• Social: Instagram / Facebook / TikTok / LinkedIn (search “Wingman Planning”)