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Episode 205

Building Brick by Brick: Nate Winkler’s 4x Founder Story

This week on The Exit: Nate Winkler, 4x founder, shares insights from his entrepreneurial journey, starting with his early exposure to business through his landscaping business in 6th grade and his parent’s real estate company.

He discusses his first major venture, Juggernaut Training Systems, and the importance of finding the right business partner, highlighting how this relationship shaped his entrepreneurial path.

He details the growth of his SaaS business, Elevar, from its challenging start to its successful exit, and how mentorship and education enabled him and his team to stay ahead, rather than constantly trying to catch up.

Nate’s advice to his younger self includes focusing on skill development alongside hard work, and building businesses incrementally rather than searching for “silver bullets.”

For more details and insights from his entrepreneurial journey, listen to the latest episode of The Exit.

Personal Bio: 

Nate Winkler is a four-time founder who has one exit in his career under his belt. Nate has been a part of 400+ client projects, has been an entrepreneur for 14 years with 3 bootstrapped SaaS products, and multiple national marketing industry awards. Nate is currently the founder of Nate Winkler Ventures which focuses on real estate investments & hospitality operations.


Website: https://www.winklerorg.com/

Nate’s Podcast: https://bxbpod.com/

LinkedIn – https://www.linkedin.com/in/nate-winkler-bb36034a/

For a Free Flippa Business Valuation: https://flippa.com/exit

The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

YOUR HOST

Steve McGarry

An entrepreneur, content creator, and investor based in sunny Tampa, Florida. In 2015, while living in San Francisco, Steve sold his first fintech startup LendLayer to Max Levchin’s (founder of PayPal) consumer finance company Affirm.

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