Oct. 16, 2026

Just Start - You Don't Need to Know How It Will Work | Keith Chandler #033

Just Start - You Don't Need to Know How It Will Work | Keith Chandler #033
Just Start - You Don't Need to Know How It Will Work | Keith Chandler #033
Austin Green | Sitting In
Just Start - You Don't Need to Know How It Will Work | Keith Chandler #033

Sitting In Podcast | Ep. 033 - Keith Chandler is a serial entrepreneur and hobbyist.


How does someone learn to take risks and grow their self-confidence? What does being raised by a single mother teach you about growing a business?


In today's episode, you can expect to learn:

- How Keith's single mom made him into who he is

- The power of reframing your perspective

- What it means to have a fear of succeeding

- What the "Slate Truck" advertising model missed

and much more!


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00:00 Intro

00:46 Keith's background

03:23 Why start a business in the first place?

05:02 How does scaling different types of businesses compare?

07:10 How do you deal with changes out of your control?

08:08 Being afraid to fail vs being afraid to succeed

08:58 Being raised by a single mother made Keith who he is

11:03 How to get over the fear of succeeding

14:13 Reframing fear into excitement

15:42 What are the hardest decisions in business?

18:24 "Put Your Aces in Their Places"

21:25 How to build trust in your employees? (Inspect what you expect)

23:40 Well-rounded vs playing to strengths?

25:43 Why sell two businesses and go back to corporate America?

28:08 The value of integrity

30:19 The power of reframing!

31:05 Why did Keith start his current business? (Plus stories)

36:53 Most people miss the niche parts of niche industries

37:38 What did Keith's mom teach him while raising him alone?

39:32 3 Reasons not to be scared of risk

41:48 Were all of Keith's changes a "level-up"?

42:34 A few more lessons from Keith's mom

44:05 How to keep the big picture in view during the tedious times?

47:06 How to let go of responsibility?

50:16 No one wants you to fail, and no one wants to do a bad job (usually)

52:37 #1 Skill for someone considering entrepreneurship

54:04 Has Keith always been a skilled communicator? (The answer might surprise you!)

55:52 How do you find good people without sinking too much capital?

57:29 How to say 'no' to an employee's request

59:52 How should someone find the "right" business to start?

01:01:00 Nuance between finding innovation and existing demand

01:03:24 Slate Trucks case study - being unique doesn't beat finding the right customer

01:07:40 What would Keith beg a young person to learn sooner than he did?

01:08:47 What do the next 5-10 years look like?

01:09:59 What does a CEO actually do?

01:11:48 Self-aware suffering or complacent simplicity?

01:13:05 How does it feel to be close to a huge goal?

01:13:57 How do you know when you're getting close to the "end"?