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January 23, 2026

The Hard Parts We Rarely Talk About

Neil Weitzman Neil Weitzman
Neil Weitzman, The Independent Operator
The Hard Parts We Rarely Talk About
7:46

Welcome to The Independent Operator, a blog series from Pavilion featuring insights for GTM leaders navigating fractional and advisory work.

Meet Neil...

Neil Weitzman is a longtime Pavilion Ambassador and the co-leader of our CAF (Consultant, Advisor, Fractional) sub-community. A seasoned fractional CRO and GTM operator. Neil brings tactical wisdom and unfiltered insights to help independent executives thrive. This article is part of The Independent Operator, Neil’s ongoing series for Pavilion.

Connect with Neil on LinkedIn | Linktree | Follow his GTM or GTMFO Substack or learn more at weitzmangtm.com


The B2B world is very good at showing progress.

New roles. Fundraises. Promotions. Big deals. Your feed fills up with polished headshots and confident announcements and from the outside it looks like momentum is on fire and your growth and your career is always moving upwards.

Independent operators see something different.

Working as a fractional CRO or CMO, or a solopreneur, puts you closer to the truth of how companies and people actually operate. You sit with and trusted founders and owners who are stretched thin, sales leaders carrying pressure they do not share publicly, and operators whose job security changes faster than their LinkedIn headline. In other words you see the truth and you feel the truth.

You experience it yourself as your revenue is not guaranteed, engagements change and the work often comes in waves.

There is an expectation that experienced independent operators should always be able to handle things on their own. After all, we chose this path. We have the background, the network, and the skill set (or at least you should, to be successful as an independent operator).

That expectation can create silence when things get hard. Many people in our space have had moments where money was tight and work and money was uncertain.

Independent Operators aren’t the only ones who have it hard - that's for sure. 
- Founders often bootstrap and barely survive.
- AEs / BDRs and marketing pros lose their jobs often and it's hard as hell to get news ones.
- CROs and CMOs job tenure is short.

For all the excitement and $ in the B2B world, it's tough as hell out there.

If you have never had to think about where the next paycheck was coming from, you are fortunate. Most people in this ecosystem have felt that uncertainty at least once.

Whether you are an independent operator, a CRO, CMO, Founder, AE, BDR or Marketing professional, if you have never had to worry about how to pay the bills, count yourself blessed. 

15 Year Old Emma

I recently read a story about a 15-year-old girl named Emma. Her mom was at the kitchen table crying over a $340 electric bill. Out of a job and broke with payday was a week away.

“Mom, what’s wrong?”

Emma's mom was honest and Emma just walked to her room, and came back and handed Mom $160 from her babysitting money.

"I’ve been saving for homecoming. But we need lights more.” Mom broke down crying.

The next day, Mom heard that Emma told her friends what happened. “My mom works two jobs and we still can’t keep the lights on. The system's broken.”

By end of day, many of Emma's friends had Venmo'd and Zelle'd $5, $10, $20 with messages like, “My Dad went through this” and “We know how this feels"

Mom's pride wanted to refuse it, but Emma said, “Mom, they WANT to help. Let them.”

The electric bill got paid. The lights stayed on. Emma taught us that asking for help isn't a weakness. It’s human.

This evolved into the "The Utility Club" - teens with part-time jobs donated $5 or $10 a month into a pool and when someone's family hit a crisis the pool gave them the money. No questions, no shame. Anonymous.

Bad things happen to good people all the time and it's nothing to be ashamed of.

A Utility Club for B2B/GTM

Emma and her friends made me think about what we could do for the B2B/GTM world. The founders, sales reps, GTM professionals who are going through it and need a hand up.

It is a big world out there and it is also a very small world at times.

Most of us know someone who has struggled mightily or someone who is currently. Your LinkedIn feed is full of "Open to Work" banners but behind those polished headshots might be a person sitting in the dark wondering how they are going to get through the next month.

Helping someone through a tough month does not solve every problem but it can create breathing room, reduce panic, and might give someone space to think clearly and move forward.

Sometimes helping someone through a tough month is everything.

That belief is what led my son Hunter and me, through the PORCH Foundation (Not for Profit), to recently launch the B2B/GTM Utility Club, to help someone going through a crisis and needs a hand up. It is modeled on the same idea Emma and her friends created. People helping people in a simple and practical way.

Here is how it works.
Every month (starting at the end of January).
Randomly.
From the list of applicants.
We will pick a name.
We will hand them the money collected.

Sometimes the best of us need a hand up during a time of crisis.

Why I Feel Strongly About This

#1 - I have had some tough times myself. I know 4 people right now who have very little money, and I am sure there are more in my network who are going through tough times. I think we can help.

#2 - Communities that support their own members create better outcomes over time. People can then take smarter risks, recover faster from setbacks, and pay it forward.

#3 - At a certain point, success stops being about titles and starts being about reputation. How you treat people. What you do when things are uncomfortable. Whether you contribute when there is no immediate return. As I get older, this weighs heavily on me.

#4 - Independent work can provide freedom and it also gives more choice. We get to decide what kind of ecosystem we are part of and what kind of operators and professionals we become. I want to be one who helps others when I can.

If This Resonates And You Are In A Position To Help

If you are in a position right now that provides you the ability to help; you can go here and send $1, $5, $20, or any amount that feels right: https://donate.stripe.com/eVq6oH1467B55KU5WD97G0r

Contributions are small, voluntary, and pooled together to provide practical support when someone needs it most.

We donated $500 to kick it off and we have already raised over $1,000 to help someone at the end of January.

A Hand Up

Needing a hand up happens to almost all of us at one time or another.

Maybe you need some help with this month’s utility bill or helping the kids with something you can’t afford but they deserve. If you need a hand up right now and are going through a crisis, apply here: https://porch.fillout.com/utilityclub

No judgement.
Anonymous (nobody but me will see your name). 
We will randomly pick someone at the end of the month and hand out the money. 

Last Thought

Things are changing so fast it is incredibly hard to keep up. None of us can predict the future and it's both exciting and incredibly scary for ourselves and our children.

Work will continue to be unpredictable and careers will remain nonlinear. That is not going to change, but what can change is how we show up for each other along the way.

See you next month with another reflection from independent operator life.

P.S If you want to help out in any way DM me. 

Topics Covered

  • Thought Leadership
  • Best Practices
  • Guest Post

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Neil Weitzman
Neil Weitzman

Neil Weitzman is a longtime Pavilion Ambassador and the co-leader of our CAF (Consultant, Advisor, Fractional)sub-community. A seasoned fractional CRO and GTM leader and founder of weitzmangtm.com, Neil brings tactical wisdom and unfiltered insights to help independent executives thrive.

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