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Modern Craftsman

399 What We Got Wrong Starting Out

Modern Craftsman

Modern Craftsman

Entrepreneurship, Education, Business, Self-improvement

4.81.2K Ratings

🗓️ 19 April 2026

⏱️ 62 minutes

🧾️ Download transcript

Summary

Nick and Tyler look back on the early years of running their businesses and talk through the mistakes, blind spots, and lessons that shaped how they work today. From underpricing and freebies to confidence, process, and figuring things out without a playbook, this episode is a straight conversation about what starting out really looks like.

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Show Notes: 
00:00 Looking Back at the Early Years
02:51 Freebies, Ghosting & Early Mistakes
06:17 First Jobs, Permits & Winging It
09:46 The Educational Tax
14:41 Getting Better Gets More Expensive
17:28 Honesty, Pricing & Client Optics
24:50 Ego, Confidence & Early Pushback
29:52 When Your Old Clients Stop Fitting
35:17 What Clients Actually Value
38:25 Why Most Builders Still Lack Process
46:03 The Playbook We Wish We Had
52:34 Why This Work Matters
57:08 Why the Newsletter Exists

Video Version:
https://youtu.be/7q6ffiowVOQ

 

Partners: 

Andersen Windows

Harnish Workwear 

Use code H1025 and get 10% off their H-label gear

 

Transcript

Click on a timestamp to play from that location

0:00.0

As you gain experience, as you grow in business, you're going to become wiser.

0:05.3

You're going to smarten up and you're going to realize that like you've been undercharging

0:09.6

and not capturing time, resources, energy, material, and you're going to get better.

0:16.9

Tyler, today you want to swing it back 10 years.

0:23.0

Take a trip down memory lane, bro.

0:25.6

Is it you DMing me about the stain color on the door I did 12 years ago?

0:30.3

Yeah, I was just getting the juices flowing.

0:32.2

It was nice.

0:33.2

I like your profile picture.

0:36.4

Speaking to a couple of people in the industry a buddy who was looking

0:40.8

to go out on his own and being away on vacation i was thinking a lot about 10 15 years ago and

0:47.3

starting my business and the struggles that i face and how much different things are now and even

0:53.5

just a lot of the insight and communication that

0:56.3

we get from people within our community who are just starting out or a few years into business

1:00.6

and how helpful it's been so I wanted to talk a little bit about when Nick started his business

1:06.8

how what things looked like when I started my business some of the struggles what we do

1:11.6

differently and just dive into that a little bit it's been a while since we've really

1:18.4

talked a lot about the past and how much things have changed but that was the goal for

1:22.3

today's podcast episode just a little bit of a blast from the past, some reflection, you know, see how far

1:28.3

we've come. This podcast is brought to you by Anderson Windows. Wait, hold on. All right,

1:33.6

so for this, Anderson, Anderson. Anderson, our connection at Anderson is Ellie Kineps. That was the original, right? Like I think

1:46.3

she went from another company to Anderson. We knew her husband, Casey, which you all probably

...

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