| 035: Knowing When to Fold

035: Knowing When to Fold

035: Knowing When to Fold

In this episode of Drop and Give Me 20, Lindsey interviews Molly Winkle and Janine Boldrin about knowing when to fold. In military-related business, we see some switching from one focus to another.

They shared their experiences as military spouses and how they came up with different and difficult decisions.

Molly Winkle is a veteran whose husband and son are on active duty and are currently deployed. She is a realtor specializing in military and long-distance relocation.

Janine Boldrin started Military Kids Life after working as a freelance writer in the military space for over a decade. She is currently the managing editor of Military Spouse. Her husband is in active duty in the Army.

Important topics they discuss:

  • [02:00] Molly’s military background and what her business is all about
  • [03:04] Janine on starting Military Kid’s Life back when she was a freelance writer
  • [03:10] Military Kid’s life as the first print magazine for military kids
  • [03:24] Janine’s family and job background
  • [04:05] Knowing when to fold
  • [04:20] How Janine felt when they had to sell the project she spearheaded
  • [05:20] Molly’s experience making a switch from one focus to another
  • [06:53] How Molly transitioned to real estate
  • [07:46] How Janine felt about closing her business
  • [09:54] When Molly realized the business is not worth pursuing
  • [11:25] The impact being a military spouse has on entrepreneurship
  • [15:00] Will they become an entrepreneur again?
  • [17:40] Tips for those who are in the same situation they are in
  • [20:58] Advice to those who are thinking about folding their business



“. . . you’d think that you just have to work harder. And it’s hard to figure out what that balance is or that tipping point of ‘Is my hard work going to catapult this or is my hard work in vain?’ and identifying that moment where you can figure out is it really just ‘I need to go a few more weeks or a few more months, or even a year, or even I put it in a year . . . it’s really not going to be where it needs to be . . . ” – Janine Boldrin

Molly Winkle on Facebook 
Molly’s Email Address: molly@mollywinkle.com
Military Influencer Conference – MIC 2018 
Military Spouse 
Janine’s Email Address: janine.boldrin@militaryspouse.com

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