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Jamie Klingman: Build Your Business So It Can Run Without You One Day

Updated: Jul 19, 2020

Special guest this episode: Jamie Klingman. Jamie was a straight A pre-med student that couldn't be around cadavers. So, she started her first company at age 22, built it up over a decade, then sold it and gained enough financial independence to start several new businesses (and a non-profit) of which she operates today. They include a real estate brokerage, a business brokerage, a publishing company, and a few other side projects - and she serves on at least two non-profit boards at any given time. Jamie and I talk entrepreneurship and mindsets for this challenging economic time.

SPONSOR: Executive Launch ( – from corporate executive to startup founder

Full Episode (YouTube):

0:17 Jamie’s backdrop is a guitar painting purchased at auction at a Big Brothers Big Sisters dinner 5 years ago

0:46 Jamie loves the music of Rob Thomas – but not as much as Bon Jovi

1:56 Jamie plays air drums to Living on a Prayer

2:39 Allen says Jamie has a really cool story that involves cadavers

3:26 Poll question: How different do you think the economy will be when it comes back?

4:04 Allen’s opening question – how much is all of this changing us?

4:17 How do we prosper in this new world that’s coming?

4:46 A lot of good things are coming from it

5:01 SPONSOR: Executive Launch ( - from corporate executive to startup founder

7:22 Clients do become bosses

7:53 Jumping into Jamie’s story

8:33 Jamie chooses pre-med - then hits a snag

11:25 She graduates and has nowhere to go

13:32 An opportunity presents itself to start a home health care company

15:54 Her company grew quickly

16:18 She realizes a shift – she was in business and was a business person

17:12 She was 22 years old and had employees quickly

17:52 Acknowledges that she had support and still made a ton of mistakes

18:07 Success is attributed to hard work and putting yourself in positions where opportunities and luck can play out

18:31 Learning from other people and being involved is hugely helpful

19:03 How Jamie hired employees

20:16 Learned what expenses were important

20:19 Somebody told her that business was conducted on the golf course so she got golf clubs - this wasn't true!

21:19 Allen says the risk Jamie took is the coolest part of the story so far

22:12 He asks if her parents were aware of what she was doing

22:21 Jamie gives her parents credit

23:05 Everyone who worked for her at first was older than she was

23:43 Business grew to a headcount of 49

24:59 Then came the big “oh-oh” moment when she thought she could sell her business

25:05 Jaime talks about the changes she had to make and the decision process to sell the business

25:18 Jamie gives credit to anyone who owns a health care company or is in that space because it is very tough

26:06 The emotional burden business owners carry in that business

26:29 Other doors were opening - maybe this isn’t where I’m supposed to be forever

26:49 Jamie shares her critical mistake - business wasn’t sale-able as long as it was so reliant on her

28:56 Allen talks about the Solopreneur Trap in his book Quit to Start

29:48 Business owners/entrepreneurs are super-heroes, that becomes a problem

30:07 Allen calls business starters/owners a freak of nature

31:55 Jamie hired an office manager and more

33:05 Her business became sale-able in three years

33:29 After she sold, she felt lost and sick - separation anxiety

37:05 The message – build your business in such a way that it can run without you

37:44 The other goal is freedom

38:55 Think about the end when you start a business

40:32 Always helpful to have somebody who’s been through it be a mentor

41:44 Jamie is now a mentor and has a mentor

42:32 Jamie’s current business – real estate, business brokering

43:40 And prior - event space and karaoke parties (because she gets bored and needs a creative outlet)

44:18 Allen questions - how would she sell somebody on entrepreneurship

44:35 You have to be willing to take risks

45:04 The benefits are absolutely freedom and flexibility

46:21 Make your way the way you want to make it

46:53 But after the risk part, there comes struggle and frustration

47:44 A guarantee to have a paycheck every two weeks versus unlimited potential?

48:59 Jamie’s philosophy on business – look for silver linings and find the win-win

50:35 Advice to give people today that are losing jobs and are anxious about this economy

51:45 Jamie’s visualization - going out on the waves…

59:24 Answering call-in questions

1:08:53 Build your reputation

1:14:44 Discussing isolation

1:17:44 Look to what we have versus what we don’t have

1:18:58 This is an opportunity to be enlightened - opportunity versus a loss

1:20:35 Jamie is excited about her new publishing company

1:22:22 People do have time to share what’s in their heads

1:27:31 entrepreneurs should always be experimenting

The Klingman Group:

Full Episode (YouTube):


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