234: Side Hustle Sales Coaching: What Do I Do and Who Do I Do it For?

Listen in on a real life side hustle coaching call with customer acquisition and retention strategist David Hutcherson (he’s the client), and sales pro Brendan Alan Barrett (he and I share the coaching duties).

On the heels of last week’s sales-themed episode, I invited Brendan on because of his sales background both with companies large and small.

We’re joined by our “client” David, who’s seeking to grow his freelance/consulting side hustle and build on his decade of experience in customer service.

127: Side Hustle Coaching: When to Pause

How do you know when it’s time to step back, take a “time out,” or stop the hustle?

There’s no spreadsheet or matrix or formula to give you the answer, but I think you know it in your gut.

And even then, there’s probably a part of me that wants to say, no, this is just “the dip” — keep pushing.

If you’ve been following along with my public coaching series, you know that Wellington has been working some insane hours at his day job.

120: Side Hustle Coaching: 10x Thinking and Standard Operating Procedures

I was able to catch up with Kathryn, one of my public coaching volunteers who’s starting a gluten free baked-goods company in Portland, Oregon.

Where we left off, things were going pretty well.

She’s been pounding the pavement doing some good ol’ fashioned cold calling to land her first clients, focusing on coffee shops in the local area. She had 2 recurring clients and around $250 a month in profit, but had just started a new job and was pressed for time.

119: Side Hustle Coaching: What it REALLY Takes to Build a SaaS Business, with Special Guest Dane Maxwell

It’s been almost 2 months since we last caught up with Wellington, one of my public coaching volunteers. Where we left off, he was working on a smartphone app for travel hackers and kicking around the idea for a software business in the home renovation estimating world.

Our last session was a rough one.

Wellington had just broken his foot and had his app repeatedly rejected from the app store for bugs that needed to be fixed. To make matters worse, his day job had become increasingly demanding and he was putting in 60-70 hour weeks at work.

109: Public Coaching Update: Rejected by the App Store!

Where we left off with Wellington, he was facing some quality control challenges with his app developer in building the Getaway Geek travel hacking app.

There was some back-and-forth after some testing and a lot of bugs that needed to be fixed. Since we spoke, those had been reasonably buttoned up and Wellington submitted the app to the App Store for approval.

Unfortunately, it’s been rejected … 3 different times.

107: Side Hustle Coaching: The Sales Process and Delivering the Goods

In today’s installment of my public coaching series I’m catching up with Kathryn, who’s starting a gluten free baked goods business out of her home in Portland Oregon.

When we last spoke, she’d just landed her first customer and sold her first $20 worth of product. Now she’s up to two recurring clients and is also contracting to make gluten-free granola for one of her customers.

103: Public Coaching Update: App Development Headaches and Brainstorming a SaaS Business

In this episode we’re catching up with Wellington, my public coaching volunteer in New York. Where we left off, he was working with an outsourced app developer to finalize a beta version of his travel hacking app for the app store.

He shared that he’d previously only ever made $0.07 online, but has the goal of earning $2500 a month by the end of 2015. One of the biggest challenges for Wellington is time; he’s been working 12-13 hour days for his day job, and making the most of his limited evening hours and commuting time.

101: Public Coaching Update: Kathryn Lands Her First Customer and Talks Next Steps

In this episode we’re catching up with Kathryn, my public coaching volunteer in Portland. Where we left off, she was starting a gluten-free cottage bakery out of her home.

The ultimate goals were to be able to leave her less-than-awesome day job and figured with a net monthly side hustle income of $1500, she’d be able to lease some commercial kitchen space and scale up her operations.

When you met Kathryn, she was pounding the pavement, calling on local coffee shops to drum up interest and had set a 2-week goal of landing her first customer.

Usually Hustling, Occasionally Social