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Entrepreneur’s M&A Journal Episode 59—Interview With Heather Osgood


Jim Cumbee and Heather Osgood walk through Heather’s experiences from sales to entrepreneurship. The mistakes you make when you first start your business to all the great things that happen as a small business owner.

Main Questions Asked: 

  • Did you buy your business or did you start it from scratch?
  • Did you spend too much time trying to fix the business you bought?
  • Did you expect to own your business for a certain amount of time?
  • What led you to decide to sell?
  • So, tell us how you and your best friend/business partner decided to sell and determine the valuation.
  • Was there any acrimony during the process?
  • As you look back on it, are there things that you would do different?
  • What would you have done differently if you had the chance to start your business over again?
  • What was the deal you made with your partner?

Key Points made:

  • Day to day I was dealing with small business owners in my job and I got a unique perspective. (1:30)
  • I thought, I would never want to be a small business owner because I saw all the challenges and struggles they went through. (2:00)
  • I owned a very successful trade show Production Company that I had for 10 years and I sold it last year. (3:24)
  • We started from scratch, we focused on Home and Garden and Health and Fitness Shows. (3:33)
  • We purchased a different production company that put on 4 different events. (4:36)
  • I wouldn’t buy it again, but I got a great experience. (5:45)
  • We worked with a business coach and he asked what our exit strategy was. We didn’t have one. (6:50)
  • There is not a lot of separation between you and your company. (8:10)
  • I hadn’t really structured the company with my life goals in mind. (8:40)
  • I got excited about new opportunities and the business became less interesting. (9:20)
  • A business partnership is like a marriage. (10:10)
  • At the end of the day, my partner said she would rather buy me out than sell. (10:50)
  • There was friction, but she is still a friend and I was very fortunate to have her as a business partner. (11:40)
  • The very biggest and most important lesson is that you should always start a business with an exit strategy. (12:57)
  • If we would have had foundational terms in the beginning then it would have made the exit much easier. (13:44)
  • I think you should decide if you are starting a business or creating a job for yourself. (15:00)
  • If it is a business, it should be something that is outside of yourself. (15:30)
  • If you have created a job for yourself, then it is not salable. (16:00)
  • You need to be clear about what is ideal for you. (16:10)
  • I am being paid out over time. (17:00)
  • I am offering 10 of your listeners a 45 minute free coaching session. (21:00)
  • Try to implement the changes you want in your business and it could change your business. (23:17)

Resources Mentioned:

How to Quit Working

How To Quit Working Podcast

For free coaching session go to:\freecoaching

Thank you for listening! Please subscribe to the podcast in iTunes and if you enjoyed this interview, leave a 5 star rating and review!


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Tennessee Valley Group

Jim Cumbee established Tennessee Valley Group to help business owners fulfill their dreams for life after business ownership. It’s a mission that his 30+ year career history had prepared him well for—in addition to being an attorney, transition mediator and business broker, Jim has been a buyer, seller, and entrepreneur. His broad range of experience gives him unique insight into how business buyers and sellers can achieve their goals.

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