10 Mistakes That Made Us Successful
Every successful entrepreneur has a list of failures they’d rather forget. In this episode of the Main Street Business Podcast, Mark J. Kohler and Mat Sorensen pull back the curtain on 10 costly mistakes that shaped their careers, businesses, and investing strategies. From IRS payment plans and failed ventures to hiring missteps and investing regrets, they share the lessons that ultimately helped them build stronger companies, make better decisions, and create long-term wealth.
Key takeaways from this episode:
• Why falling behind on taxes can create years of unnecessary stress
• How knowing when to shut down a business can be a winning move
• The hidden cost of employee turnover and poor onboarding
• Why reading the fine print can save you hundreds of thousands of dollars
• When entrepreneurs should pivot instead of pushing harder
• The dangers of chasing too many opportunities at once
• How delegation can unlock the next stage of growth
• Why business owners need assets outside their core company
• The financial risk of increasing your lifestyle too quickly
• How mistakes become your greatest source of business wisdom
The reality is that entrepreneurship is not about avoiding mistakes — it's about learning from them faster than everyone else. If you've ever felt behind, made an expensive mistake, or questioned a major decision, this conversation will remind you that every successful entrepreneur has been there too!
CHAPTERS:
0:00 Intro
0:34 The Biggest Mistakes We Made That Eventually Helped Make Us Successful
2:17 Mistake #1: Falling Behind on Tax Deposits
5:50 Mistake #2: Trying to Keep a Business Afloat When It's No Longer Working
13:05 Mistake #3: Not Paying Overtime Based on a Handshake Agreement
15:29 Mistake #4: Neglecting the Value of Training and Retaining Good Employees
19:33 Mistake #5: Not Reading the Fine Print in Loan Documents
22:55 Mistake #6: Building Too Narrow of a Brand on Social Media
29:13 Mistake #7: Trying to Do Too Many Things at Once
33:32 Mistake #8: Struggling to Hire an Assistant
38:24 Mistake #9: Not Taking Early Business Profits Out to Invest in Retirement Accounts
40:55 Mistake #10: Upgrading Lifestyle Too Early
48:42 The Moral of the Story: You Will Make Mistakes