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Side Hustle School

Ep. 3294 - Q&A: “I’m offering executive coaching at a high price…”

Side Hustle School

Chris Guillebeau / Onward Project

Business, Careers, Entrepreneurship

4.83.3K Ratings

🗓️ 7 January 2026

⏱️ 6 minutes

🧾️ Download transcript

Summary

Today’s caller is on their second attempt with a coaching service for busy executives. It’s a big-ticket item, but the first round didn’t go very well. What should they change for take two?

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

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Transcript

Click on a timestamp to play from that location

0:00.0

It's going to be a big year. And January is when so many of us set goals for our business,

0:04.8

for all the things we want to achieve. And in a small business or a side hustle, even,

0:09.6

cash flow can make or break you. So if your money gets tied up, if your tools don't connect,

0:14.1

every decision feels unnecessarily stressful. Maybe it's time to switch to Intuit QuickBooks's

0:20.0

money management tools. Big shout out to QuickBooks,

0:22.9

our sponsor, start the year with confidence about your goals. Learn more at quickbooks.com

0:27.9

slash money today. Again, that's quickbooks.com slash money. Terms apply. Money movement services

0:34.7

are provided by Intuit Payments Incorporated, licensed as a money transmitter

0:38.2

by the New York State Department of Financial Services.

0:43.6

Lemonada

0:44.2

Today's caller is on their second attempt with a coaching service for busy executives.

0:57.9

They've got this idea. They put some work into it. And it's a big ticket item, which is good.

1:03.4

It's a lot easier to sell, or at least you need fewer clients, fewer customers if you're

1:07.9

selling something at a higher price than at a very low price, especially

1:10.8

in the world of coaching. But as I said, they're on their second attempt here. The first round did not

1:15.2

go very well. That's totally normal, of course. So as they regroup and try again, as they go for

1:21.7

take two, what should they change? A very helpful question to ask, if you're ever in that situation

1:26.3

of your first attempt, doesn't completely meet your expectations or get you the results that you want. Okay, let's go back and regroup and try again, but we'll change some variables. You don't want to just keep trying doing the same thing that's not working. But if you make some adjustments, some tweaks, perhaps that will in fact be helpful for you. So I'm going to do my best to

1:44.4

be helpful to this caller. Their name is Sean. Welcome to Saitocile School, by the way. I'm

1:48.3

your host, Chris Gillebaud. The detailed question from Sean and my answer coming right up.

1:55.7

There are lots of people right now focusing on hitting their protein goals. Maybe they want to

2:00.2

help build and maintain muscle

...

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