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Issue #13: The 5-Minute Research Mistake That Almost Cost Us Everything

From Face-Plant To Jackpot

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Welcome to another episode of "Greg Builds Multiple Income Streams While Trying Not to Face-Plant in Public." (We're working on a shorter title.)

The other day, I messaged one of my long-time mentors. Among other things, I said: "Really busy hustling and selling!"

His response? The same wisdom he dropped on me 15 years ago, which I've carried like a rare item in my entrepreneurial inventory ever since:

"Keep doing both, whilst having fun. Look to help people, rather than earn money, when you do the money just flows."

This hit me right in the feels because it aligns perfectly with my core belief: Build your ideal life first. Then, figure out the business stack that supports it.

Think about it - most people do this backward. They build careers (me included) and try to squeeze life into whatever time is left over. But here's what I've learned: Start with the life you want, then build lean, multiple, profitable side hustles that fit into it. Sometimes, that means grinding out side hustles during your 9-to-5 years, knowing it'll pay dividends when you switch to your chosen 5-to-9.

Be the turtle. 🐢 

Speaking of building strategically, today's newsletter is packed with entrepreneurial cheat codes I had to learn the hard way.

Here's your TL;DR (but please keep reading - my coffee addiction needs funding):

Today's Power-Ups:

  • A closed door is sometimes just a tollbooth in disguise

  • A "no" might really be a negotiation opener

  • The actual decision-maker isn't always at the table

Let's dive into how a casino's "no" turned into something way more interesting than we expected...

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Speaking of which – if you're joining our adventure, here's what you missed in our latest episodes:

Instant Replay

If you don’t know us, check out the start of last week’s issue when we re-introduced ourselves to all the new readers: Issue #12: Three Easy Steps To Get Thrown Out Of A Convention 

Picture this: A month ago, I'm sitting in my home office (spare bedroom), feeling pretty smug about my entrepreneurial journey (the self-crowned ‘#1 Entrepreneur in Training’), when my wife Kirsten drops a franchise opportunity in my lap. My immediate reaction? Pure snobbery. "Franchising seems a bit... pedestrian," I scoffed, worried about my newsletter street cred. (I know, I know... I'm still cringing, too.). Also, I was super busy being an ‘ADVISOR’ 😓 (so smug).

Season 9 Nbc GIF by The Office

Gif by theoffice on Giphy

But here's the thing about being married to someone smarter than you – sometimes they see opportunities you're too proud to notice. While I was busy trying to look like a "real entrepreneur," Kirsten was analyzing actual market opportunities. She found chargeFUZE - a network of portable phone charging stations where you can grab a battery pack, charge your phone while you move around, and return it when you're done. Brand new for us Canadians.

Fast forward through several weeks of research, market analysis, and me eating a healthy serving of humble pie, and here we are: Calgary's exclusive ChargeFUZE partner, proof that sometimes the best opportunities don't need to be revolutionary – they just need to solve real problems.

Armed with our venue assessment checklist and Kirsten's killer product demo skills, we started hunting for prime locations across Calgary. First stop? The city's entertainment venues, where dying phone batteries are as common as spilled drinks. Little did we know our initial venue visits would teach us more about stakeholder mapping and corporate politics than any MBA program ever could...

Buckle up, friends. Today's story is about what happens when you let go of your entrepreneurial ego and embrace the power of proven business models... 🎮

The Casino Chronicles

When Your First Big Win Turns Into a Royal Flush (And Back Again)

SCENE: Greg and Kirsten's home office, post-casino meeting. Empty champagne glasses on the desk, and Kirsten's perfect product demo video is playing on repeat on the laptop. Greg is mid-tweet about their success.

KIRSTEN: (grinning) I still can't believe how well that went! Did you see their faces when I showed them how fast someone could grab a charger and go?

GREG: (typing on the phone) "Crushed our first ChargeFUZE demo! Big thanks to..."

KIRSTEN: Are you humble bragging on social media already?

GREG: It's not bragging if it's true! Besides, you basically ran a masterclass in seamless user experience. Scan, grab, charge - you made it look effortless.

Phone rings. Greg's entrepreneurial swagger visibly deflates as he listens.

KIRSTEN: (watching Greg's face fall) What is it?

GREG: (hanging up) Well... remember how we were just celebrating our first big win?

KIRSTEN: Let me guess - the owner wasn't as impressed as the marketing team?

GREG: (slumping in chair) Apparently, the slot machines have wireless charging. Which nobody knew about. Including the marketing team. And now the owner is...

KIRSTEN: (cutting him off) Wait. The managers didn't even know about their own wireless chargers? This isn't about us at all.

GREG: (reaching for the champagne bottle) Should we un-pop this?

KIRSTEN: (thoughtful) You know what's interesting? He's not mad about our product. He's mad about internal communication. That's a completely different problem.

GREG: (perking up) A problem that might need a Mills team solution?

KIRSTEN: Now you're thinking like a business person instead of Danny Ocean.

GREG: (already typing new tweet) Should I delete the humble brag?

KIRSTEN: Keep it up. Something tells me this story isn't over yet.

You know that feeling when you're absolutely crushing it at the blackjack table, counting your chips, planning what you'll do with your winnings... and then the dealer pulls a 21 out of nowhere?

Yeah, that just happened to us. But instead of cards, we were playing the entrepreneurship game. And let me tell you, the house always wins – just not in the way we expected.

Setting Up Our First Big Play

Picture this: Your boy Greg and the real brains of the operation, Kirsten, walking into a casino with our shiny new chargeFUZE charging station. Confidence level? Higher than a poker player with four aces. We had:

  • A perfect location spotted

  • Meeting setup with all the key managers

  • Kirsten's killer product demonstration was ready (seriously, you see how fast she makes that rental process look)

  • Trial placement being considered

  • One entrepreneur having Ocean's Eleven fantasies (that would be me)

The Flop (Poker Term, Look It Up)

Everything was going perfectly. Kirsten crushed the demo - making the whole scan-and-go process look smoother than a casino dealer's shuffle. The managers loved it. The station looked sleek and professional. We even had that entrepreneurial swagger going – you know, that "we're-actually-doing-this" energy that makes you feel invincible.

And then...

Plot Twist: The Boss Battle We Didn't See Coming

It turns out the casino owner didn't know about our trial. That’s usually fine; we can re-do it. But no, he didn't realize something else – that his managers did know the slot machines had wireless chargers built in. WIRELESS CHARGING…we are the wireless charging gods…

Record scratch. Freeze frame.

"Yup, that's me. You're probably wondering how I ended up in this situation..."

John Mulaney GIF by Vulture.com

Gif by vulture on Giphy

The Royal Flush (Again, Not the Good Kind)

The owner's reaction wasn't about us. It wasn't even about the charging station. It was about his managers not knowing about features in their own slot machines. Our beautiful trial became collateral damage in an meno.

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7th Inning Stretch: here are a few things to play with this weekend:

I am constantly inspired by my mentor (I wish he were 😔), Andrew Bolis (he doesn't know who I am 😭), so I will pass along some of his wisdom this week. I am working to be your Andrew Bolis…but you know what…it takes time. I’m trying…and I know you all like links… but I am so busy, so:

Picture Julia Roberts (←but me)

Don’t forgetI am just a guy, standing in front of a girl you, asking you to love like me my newsletter.”←  Notting Hill (ish)

Here is some of Andrew’s recent wisdom on side hustles:

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Big Bonus:

Read my Brother-In-Law’s recent Medium post, “15 lessons from three decades in Tech.” he is the real tech entrepreneur. Read here.

Back to the real lessons….

The Side Hustler's Guide to Corporate Politics: Lessons from the Casino Floor

Problem #1: You need to know the PEOPLE (as best you can)

Walking out of that casino, we thought we had it made. The managers loved us, the staff got it, and the demo was perfect. But we completely missed the power players behind the scenes. Classic rookie mistake.

The Solution: Power Mapping

Before any pitch, map out these key players:

  1. Decision Makers

    • Who can actually say "yes"?

    • Who holds budget authority?

    • Who needs to sign off?

  2. Influencers

    • Who has the decision maker's ear?

    • Who can champion your cause?

    • Who might resist change?

  3. Implementers

    • Who will actually use your solution?

    • Who needs training?

    • Who might be disrupted?

    • Do Even MORE Research (The Intel Strategy Below 👇)

Action Steps

Research, Research, Research…have you heard of the internet..and AI

✓ Create a simple stakeholder matrix:

Problem #2: You Need MORE Research: The Intel Strategy

We did some research, but there were a lot of hockey games on TV at the same time. 😳 

We knew people needed phone charging. We had the stats, the user stories, and even the pain points. But we missed the existing solutions hiding in plain sight. Those sneaky wireless charging slot machines? They weren't in any of our competitor research. Perplexity can only do so much.

The Solution

The Deep Dive Framework

  1. Visible Competition

    • Direct competitors

    • Similar solutions

    • Upcoming market entrants

  2. Hidden Competition

    • Built-in alternatives

    • Workarounds people use

    • Future tech developments

  3. Environmental Scan

    • Industry trends

    • Technology shifts

    • Customer behavior changes

Action Steps: The 5×3 Research Method

Ask 5 different types of people in your target market 3 different questions; here is an example from the Casino.

Problem #3: Internal Politics Matter (The Corporate Game)

Our charging station became a pawn in a larger game of corporate chess. The owner wasn't really mad about our solution – he was mad that his managers didn't know about existing features in their own machines.

The Solution: Be Aware

Warning Signs to Watch For:

🚩 Enthusiasm that seems too easy

🚩 Quick agreements without questions

🚩 Lack of push-back on pricing

🚩 Nobody mentioned the big boss

Action Steps: Politics Are Really Hard 👉 Advanced Homework

  1. Understand the Ecosystem

    • Map reporting relationships

    • Identify unofficial power players

    • Note recent changes/tensions

  2. Read the Room

    • Watch body language in meetings

    • Notice who defers to whom

    • Track who asks what questions

  3. Play Chess, Not Checkers

    • Plan multiple moves ahead

    • Consider all potential reactions

    • Have backup strategies ready

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Problem #4: Emotions Suck

Sometimes, initial rejections are harsh, and it feels like the game is over. However, by staying flexible and thinking strategically, we found new opportunities within the same venue.

The Solution: The Silver Linings Playbook (The Pivot Strategy)

  1. Segment Your Solution

    • Break into smaller pieces

    • Target specific areas

    • Create phased approach

  2. Find the Gaps

    • Identify underserved areas

    • Look for unique use cases

    • Spot infrastructure gaps

  3. Build Strategic Bridges

    • Connect with champions

    • Solve immediate pains

    • Create quick wins

Action Steps: The Opportunity Matrix

Create this for every opportunity:

Summary: Implementation Guide

Before Any Pitch:

  1. Complete the Stakeholder Matrix

  2. Run the 5×3 Research Method

  3. Create your Politics Map

  4. Prepare your Pivot Options

During Meetings:

  1. Watch for power dynamics

  2. Note unexpected objections

  3. Identify potential champions

  4. Look for hidden opportunities

After Each Attempt:

  1. Update your frameworks

  2. Document new insights

  3. Adjust your strategy

  4. Keep building relationships

Bonus: The Quick Recovery Checklist

✓ Document what you learned

✓ Update your pitch deck

✓ Revise your target list

✓ Adjust your approach

✓ Keep relationships warm

BREAKING UPDATE: Plot Twist - The Saga Continues!

Just as we were about to publish this story, something interesting happened. That "no" we got? Turns out it wasn't exactly a "no" – it was more of a "let's talk revenue sharing."

Insert "The More You Know" rainbow here 🌈

Here's what we're learning about doing business outside the corporate matrix:

  • A closed door is sometimes just a tollbooth in disguise

  • A "no" might really be a negotiation opener

  • The actual decision-maker isn't always at the table

Moving Forward: The Next Hand

We're heading back to the negotiating table this time:

  • With revenue sharing options ready

  • Prepared to talk about percentages

  • Armed for the real conversation

  • Ready for the actual decision-makers

THAT’S A WRAP

Remember: In business, like in poker, it's not about winning every hand. It's about staying in the game long enough to win the ones that matter.

Greg "Always Hit On 18" Mills

P.S. If you've ever had a "no" turn into a "let's make a deal," hit reply with your story. I could use some negotiating inspiration right about now!

P.P.S. Lesson learned: Maybe wait more than 37 minutes to humble brag about your wins on social media. But also maybe don't? Because sometimes those "premature" celebrations lead to interesting conversations. (At least that's what I'm telling myself as I leave that tweet up...)

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