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From selling La Crosse’s Dublin Square to visiting Dublin with Matt Boshcka

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Matt Boshcka, a remarkable serial entrepreneur, who has worn many business hats in the La Crosse area, joins Bizcast Greater La Crosse.


Bizcast comes out Friday mornings and can be heard online here, or by subscribing to Bizcast Greater La Crosse wherever you get podcasts.


Boshcka shares his journey from growing up in a humble setting to owning various successful businesses, including Cannabis Depot, Dream Vacations, and a travel foundation for victims of domestic abuse.

Boshcka also discusses his business philosophy, the importance of having exit strategies, his passion for travel, and his new venture into men’s health through Game Day Men’s Health.

Learn about the highs and lows of his entrepreneurial journey, his belief in giving back to the community, and his relentless pursuit of happiness and self-improvement.


00:00 Introduction and Opening Thoughts
00:22 Welcome to Biz Cast Greater La Crosse
00:31 Meet Matt Boshcka: The Serial Entrepreneur
00:43 Matt’s Business Ventures
02:35 From Humble Beginnings to Entrepreneurial Success
04:18 The First Business: Smart Health Media
06:14 The Importance of Exit Strategies
08:21 The Value of Taking Risks
11:39 Community Support and Entrepreneurship
17:12 Travel and Business Synergy
19:57 Challenges in the Restaurant Industry
21:14 Impact of Inflation on Food Costs
22:25 Owning and Transforming a Golf Course
23:16 Forming Business Partnerships
23:57 Deciding When to Sell a Business
24:34 Opportunities and Investments
25:51 Introduction to Game Day Men’s Health
27:34 Personal Interests and Business Alignment
30:05 Community Involvement and Rotary Membership
31:43 Franchising Experience
34:29 Future Plans and Personal Growth
36:30 Closing Thoughts and Reflections

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