I Almost Didn’t Make It As A Business Coach

This past week I celebrated 5 years as the owner of Good Advice and the host of the Good Advice Podcast.

Unironically I think I started off as a business coach really not knowing much at all about business.

I had done just over $200,000 in sales at my previous job and I naively thought:

Hey – this business stuff is pretty easy. Why not keep doing it?

Truth be told, when I was a few months deep in Good Advice and hadn’t made a single sale, describing it as a wake-up call would be putting it lightly.

Every great television show starts with its first episode known as the pilot episode.

In this, characters are undeveloped and plot threads are nonexistent.

Well, running Good Advice was basically a pilot episode.

But really not one for a hit new show… In fact, the early version of Good Advice was pretty disastrous.

Many people don’t know the origin story of The Big Bang Theory, which held its position as the #1 sitcom on television for nearly the entirety of its eight year run.

Even some of its lowest viewership saw nearly 20 million people watching each episode.

Prior to all of that – the Big Bang Theory started with an awful pilot episode.

In fact, it was so bad that television studios wanted nothing to do with it.

Before becoming a major hit, the popular show saw itself getting completely rewritten from the ground up.

Characters were redesigned and one central figure was written out of the show entirely.

These bold changes eventually led to its title spot on the CBS Network, where it would remain so prolifically that it would eventually get its own spin off show.

… let me be clear that I am in no way implying that there’s any sort of future like this for Good Advice.

I’m only mentioning it because – like The Big Bang Theory – my business coaching company started out as a total trainwreck.

Unlike the Big Bang Theory… I didn’t become insanely rich with millions of followers week to week.

Kind of an important detail, I guess.

I was struggling as a business coach

A lot went wrong in those early days of Good Advice.

Or in other ways, there were many early surprises…

One surprise was on the literal first day of my business, when my wife told me she was pregnant.

We had been trying for several months, which seems like an important detail before quitting a salaried job and jumping off into the open ocean of entrepreneurship.

That same week, I spent money I didn’t have hiring a digital marketer whose ad came across my feed.

Frankly, I was too naive to really know what I was getting into – but his salesperson assured me that he would be working directly with me and would get my business to earn six figures and beyond in no time.

Sounded like a great plan to me.

As you can probably guess… it didn’t work out as planned.

I was endlessly encouraged to rent flashy cars to impress my would be customers – something I felt was deeply dishonest and couldn’t go through with – to urgently being told I need to spend more on Facebook ads if I wanted to see any return…

Before I knew it, I had spent $15,000 and had nothing to show for it.

Worse, when I asked for a refund, I was threatened that I’d be taken to court, and I at least knew I had no clue how to deal with that.

Meanwhile, I had started the Good Advice Podcast.

I was passionate about business, but since I didn’t have any customers, the podcast was the outlet for me to talk about something I really loved doing.

I just wanted to help people and this was my outlet.

Unfortunately, while I was burning through cash for my business, the podcast wasn’t doing much better.

Those early episodes had maybe a handful of downloads. Most were probably me and my wife and the random friend who would unintentionally describe an episode as, “surprisingly good.”

Somehow, there was always that next customer who would appear just in time to make the next payment.

But I didn’t understand customer churn.

Heck, I didn’t even understand what I was selling or how to price it.

So customers came and went.

18 months later when it finally felt like the business was starting to take off, a worldwide pandemic brought Good Advice to a grinding halt.

One of my best customers – a local hospital – called me on Day 1 of COVID to put the contract on an indefinite hiatus, essentially canceling our contract.

I was still in the hospital with my daughter who had just been born.

And with no family support who lived in town, I was juggling being a new dad while also running a business during pure economic anarchy.

So saying I almost didn’t make it as a business coach is putting it lightly.

Something had to change.

Like I mentioned, this past week I celebrated five years of Good Advice and the Good Advice Podcast.

With that, I’m appreciating ending my most profitable quarter ever, in addition to a podcast that’s earned nearly $20,000 this year in advertisers alone.

Looking back, even the journey from Year 2 to Year 5 feels like a COVID-induced blur.

What changed?

For starters, I had to learn to love selling.

To be clear, I was never averse to sales.

And like I mentioned, at my previous company, I had done over $200,000 in sales the year I left.

So I knew something about sales.

I think subconsciously though, I so badly wanted to avoid being that digital marketer who I felt like had not only given me bad advice, but who also had really built his business on dishonesty.

Through all the years, I knew I didn’t want to be that.

So instead of leaning into the sale… I would pull back.

Entrepreneurs who miss the chance to ask for the sale.

Then, I’d wait.

Wait for the reciprocity to kick in…

Wait for the timing to finally be right…

Frankly, I would wait for God to answer my prayers and bring me more customers…

It really wasn’t until my 2nd child was born that I realized what I was doing wasn’t working.

I had great customers.

I was doing good work.

But I was always killing myself trying to get that next sale.

Bills were still getting paid but I was deeply dissatisfied by the impact of Good Advice.

As a business coach, my vision involved impacting thousands of business owners, not hundreds.

My scope of impact was the biggest clue to me that something had to change.

To make it as a business coach, I had to learn to love selling. 


My wife, who had always been the ultimate encourager, began to ask after my son was born:

“Oooooookay, so what are we doing?”

For the cracks to show in her optimism, I knew it meant she was feeling the burnout of entrepreneurship.

At the end of the day, I wanted to care more about her and her well-being than potentially upsetting someone by asking them to buy from me.

In some ways, I tapped back into that salesperson from a few years prior.

I began to be more bold and decided to make sales part of my regular routine.


My fear of becoming that sleazy salesperson was keeping me from one of the most important parts of my business.

So instead, I resolved to sell every single day of my business.

Slowly but surely, the momentum started to be more tangible.

There’s an old adage in one of my favorite books Good to Great that talks about this momentum in the form of a flywheel.

A flywheel takes so much effort to get started… but once it gets going, it can be hard to stop.

My business needed that effort… as grueling as it felt sometimes, in order to really develop unstoppable momentum.

With this, I was also realizing the ambiguity of my business and what exactly I was selling, a flaw that in hindsight is fairly common for a business coach.

So I began to productize my business, boiling down my work into definable offers as best I could.

Part of this came through a close friend who had become somewhat disinterested with his SEO business and invited me to take it for a spin.

Little did I know that this would be a majorly defining mechanism to the kind of work I would begin doing.

The other offer came through the podcast.

Through five years, I had never stopped recording and posting new episodes.

This would eventually lead to a conversation with a podcast guest – Rick West – who basically asked me,

“Why the heck haven’t you monetized this thing yet?”

I didn’t have an answer – and seeking to respond to that question opened up another pathway entirely.


Consistency Beats Insight Every Time

I’ve joked that the podcast is called Good Advice, but not “Great Advice”.

I do think it’s great advice, but people who know me know that I try to never take myself too seriously.

When I began thinking about monetizing the podcast, I’m surprised how easy it was.

It turned out that people listening to the show were already primed to buy.

Some had listened for months, and for them, the trust was enormous.

In other cases, people saw how well the podcast had done as a side hustle.

With listeners in 60+ countries and nearly 400 episodes, I began coming across other people who wanted to start their own podcast.

I wasn’t some longtime “podcast producer”.

But it turned out there was tremendous value in the highs and lows, and successes and failures in 5 years of running a show.

One of my more recent customers explained to me, “You obviously have learned a lot and I’d rather pay someone who’s actually doing it.”

I think consistency doesn’t get enough attention in the sales world.

Many content creators for example are looking for that one viral post that will catapult them into the limelight.

Its why I’ve known people who’ve talked about spending literal hours trying to craft that perfect post.

They’re all in one trying to make it happen by showing up one time, rather than understanding the power of showing up again and again.

It dawned on me early on that I really didn’t need to be the absolute best to make it as a business coach.

I just needed to show up every day.

This wasn’t my insight but my dad’s.

My dad was a legendary attorney, having done a career of 50 years.

He was much too humble to describe himself that way, though.

Instead, he pointed to his monthly newsletter that he had sent consistently for years.

When talking about his competition, my dad never bragged about himself or his skillset, even though his giftings were clear.

He joked that the newsletter let his customers know that he hadn’t died yet and was still around.

I knew there was something to be said about this for my own business, and sure enough, it became a major selling point for helping others launch their podcast.

Plan for the Ten Year Game

All this to say… 5 years later with Good Advice, I can honestly say this is the hardest thing I’ve ever done… and I was a high school teacher!

What would have made it easier would have been understanding what kind of path I was about to take.

Social media (and that mentioned digital marketer) convinced me that success comes in 30 days.

In actuality, the road of entrepreneurship is thousands of miles long.

There are some weeks that the momentum is so tangible that you’ll breeze through hundreds of miles of roadway.

And there are some days that you are so embattled to keep going that you move only inches.

When you understand the length of the journey you’re on… you give yourself grace for not being where you want to be yet.

Better yet, you stop blaming yourself for your lack of progress and instead protect a space for you to ideate, explore, and ultimately create.

I’m excited for what I’m creating with Good Advice and the Good Advice Podcast

Thanks for being on this journey with me, and I wish you well on yours.