Jamie Gruber Blog/Newsletter/My $21,000 Mistake… and How To Avoid It

Thursday, March 09, 2023

My $21,000 Mistake… and How To Avoid It

December 6, 2022 Newsletter.

Leaving my job came with an incredible sense of freedom. I’m an action taker. I’m better in motion, breaking things along the way and out of chaos creating progress. Moving fast and furious has value but also comes with drawbacks. This was one of them and how you can also avoid making the same mistake as a mid-life entrepreneur.


I have had this mantra for two years now and honestly, I’m just now learning that it’s too broad an objective. 2023 will come with specificity, but more on that later. In leaving my job, I could just taste the unfettered ability to create, provide value, tell stories – all without the concern that it gets back to someone at work that shouldn’t see it. If you’re on this email, you’ve seen consistent and steady growth of my brand, but hopefully me as a person.

Part of what I needed was guidance and direction. At this point in my life, I’m a big believer in coaching and consulting to shorten the gap between my current status and the desired goal.

What I feel I do well is authentically and genuinely tell my story. The highs and lows. Across platforms I have 30-40,000 followers. Certainly not the type of following many in my space have, but I’ve been able to make a living with that following because I truly seek to add value and it comes through. So it stands to reason that 10x the following = 10x the impact. And 10x the impact means financial security. Therefore, ‘build my brand’ is a logical goal statement.


Shortly after I left my job, my ‘move fast’ mind was ready to act. Forget down time and breathing for a minute – let’s fucking go!! I found someone with a large following who also worked with major brands that you and I have heard of and had a major role in their growth. I read the book, took the course and decided getting directly coached would be the best move I could make.

I reached out to this person’s team via their website and talked about options. There was the ‘done for you’ option at $50k+ or the ‘done with you’ option for $21,000. I went with the latter and got very little explanation as to what was offered and just said yes. Swipe – boom! $21,000 spent.


For my investment, this consultant and his team did everything they said they would. The offered exactly the type of support they offered. I had access to the consultant directly and was able to outline my desires and they produced a strategy for me. It included not only tactical advice but also communication profiling. This let me see where I communicate with influence and how to accentuate that and also where I communicate that may be a turnoff for the majority and how to mitigate. In addition, they reviewed my work after a few weeks and provided additional guidance. Lastly, they brought me into a group for a couple of months that let me sit in on weekly live feedback given to me and/or other brands involved in the group. Pretty robust!

You’re smart people – you’re probably thinking ‘you said you made a $21,000 mistake in the headline, and that you paid this consultant $21,000 – but that the consultant did what sounds like a great job .. so what gives?’ More on that in the key takeaways below.


Going into 2023, I have a much more distilled objective than’ build my brand’. I’m focusing on YouTube since the platform serves my ‘long form’ natural nature more than 1 minute videos on Instagram. Doesn’t mean I won’t be using other platforms, but I need a focus for me and my social media team – and YouTube growth gives me a clear focus. The objective is 100,000 subscribers by the end of 2023. By the way, you can help by simply clicking here and subscribing

I didn’t pay $21,000 to some guru this time though. Instead, I paid $55,000.

‘Jeez Jamie – do you never learn?’

Calmate gente! (working on my Spanish)


#1: Hire Someone With Experience and Results … but you need ONE MORE THING!

When I hired the $21,000 consultant, I didn’t spend any time with him before hiring him. His experience was and still is impressive. He’s effective at what he does. After hiring him and jumping on my first call, dude didn’t crack a smile, didn’t talk for long periods of time while he took copious notes – it was fucking awkward – for me! While experience is important, and past results matter a ton also, you have to ask ‘is this someone I would enjoy hanging out with’? It’s the same when hiring an employee. Had I known his personality, I would have passed. I need to enjoy my work – not feel like I need to mute myself and my way of being.

#2: Take Some Time After You Quit

Anyone on the doorstep of leaving their day job gets the same advice from me. In fact, it’s the same advice I was given and didn’t heed. I don’t regret it (because I don’t believe in the word) but hindsight gives me clarity. TAKE TIME AWAY!! I was JUST out of my W2 when I hired this consultant. My engine was running with employee gas. I made the hire because I could ‘logically’ explain it to others rather than because I just like this guy. I’m a ‘feeler’. I go with my gut and that has ALWAYS served me. But when you have bosses, you need to at least sound ‘reasonable’ and ‘logical’ with every decision you make. If I were explaining my $55,000 hire to myself as my own boss, I’d say ‘my objective is to grow my brand, this guy’s a branding expert who has results .. and FUCK he’s a good dude to work with. We connect’. Doesn’t make me right and Corporate wrong – but it’s right for me .. and that’s what’s important.

#3: Co-Workers Will Root For You To Fail

Sustained success after W2 life is the result of being raw and vulnerable. I share missteps like the above often and it’s extremely cathartic. It’s a foreign concept for the standard employee to be open, honest, and authentic. You don’t show weakness in that world. In fact, many former co-workers would reach out with ‘are you ok?’ if I shared a down moment on my platforms. Much of that was pulling for my demise. Not out of spite or hatred, but out of fear. If I ever tucked my tail between my legs and got a job, it would offer a collective sigh of relief to the hundreds of people who strongly desire a different life but are convinced they can’t make the leap. Order would be restored and a neural pathway would be DEEPLY carved around staying ‘safe’ at work. I’ll admit -that drives me a bit. But a lesson for you as a future mid-life entrepreneur is to always default to authentic and don’t be afraid to share.

#4: I Didn’t Actually Lose $21,000

The title of this newsletter is misleading. I didn’t make a mistake. I learned a lesson. Period. As adults, most of us share similar stories. Go to school, get grades and do homework, maybe do the college thing, get a job. Nowhere in that ascension model is there room for failure. Failure is fully synonymous with negative consequences. Beaten into us (figuratively and perhaps literally) was the need to stop fucking up. That we’re throwing our life away. That we have to try harder. Parents yelled at bad report cards, teachers looked down their noses at you and congratulated the A in the room, guidance counselors warned of your inability to get into college, bosses threaten to demote or fire you. I had to reframe my relationship with failure as a REALLY good thing that teaches me lessons once I made the leap. By being authentically me, vulnerable, and being willing to fail, I can brush off a $21,000 loss and take the lessons I need. There’s more where that came from and being me has been profitable.

NEVER forget how valuable you are!

CALL TO ACTION: Screenshot the key takeaway that landed for you and tag me in a story on Instagram so I can see what’s working for you.


Tribe of Millionaires Podcast Episode
✯ 2023 is around the corner and the time to prepare is now - not in the new year. This episode is a solo podcast where I talk about 3 ways to attack 2023 and beyond. I hope you enjoy and would appreciate a rating and review.

A Podcast/Book I Love
✯ I was introduced to a book by Phil Stutz called ‘The Tools’ by former MLB All Star Sean Casey. When an accomplished guy like that suggests something, I listen. We’ve had fun chatting about it. Now, Jonah Hill has released a documentary on Netflix called Stutz which is AWESOME. I’d suggest watching first and reading the book second.

Lesson from Living Abroad
✯ The cost of labor is much cheaper here and I briefly shared this in a YouTube short that got a lot of negative comments. The lesson is how little we know as Americans or Canadians about life in countries like the Dominican Republic. We pay $500/month for a full time housekeeper (plus $300 for a weekend/evening part time one). That is actually above the going rate for this work. Some Americans with limited context believe the housekeeper is being hurt in some way. In actuality, people like me coming down here help the housekeeper earn additional income than they would otherwise (and we pay for food, we pay for health care and other things). Who is hurt is the working class Dominican native single mom who now can’t afford the help because the help is going to the ex-pats who pay more. Odd circumstance I know, and I can’t begin to explain this in a way that will satisfy everyone.

Shit I Find Funny
✯ This reel may be the funniest thing I’ve seen in all of 2022!!!

If you’re not already in Emerge and Ascend and want to be part of our Emerge Supercharged relaunch in 2023, join the waitlist here!! The objective is to get you unstuck, clear on vision and goals, and provide a concierge level experience to introduce you to your future self!

Until next week

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